Category: 3286-55-3

Nakazawa, Junichi; Watatani, Mitsuo published the artcile< Pyrimidine derivatives. II. Transetherification in pyrimidine derivatives>, COA of Formula: C5H6ClN3O, the main research area is .

Transetherification reactions of 2-methoxy-, 2-ethoxy-4-amino-6-chloropyrimidine, and 2,6-dimethoxy- and 2,6-diethoxy-4-aminopyrimidine at the alkoxy groups at 2- and 6-position by the treatment with NaOMe or NaOEt were investigated and found that the 2-position was more reactive than 4-position and the MeO group more readily underwent transetherification reaction than the EtO group. In 5-substituted pyrimidines with an electroneg. group, the MeOH at 2-, 4-, or 6-position was readily eliminated owing to its further higher reactivity. Manufacture of the following new compounds was also described: a mixture of 38.4 g. barbituric acid 24.3 g. KCN and 144 g. urea was melted at 143-8° 4 hrs., then cooled to 100°, 240 cc. H2O added, stirred 30 min., cooled to below 50°, acidified with HCl, and filtered to give 56.5 g. 2,4,6-trihydroxy-5-pyrimidinecarboxamide (I), fiberlike crystals, m. above 360°. I (8.6 g.) was refluxed with 61 g. POCl3 and 6 g. PhNMe2 1.5 hrs., decomposed with ice, extracted with C6H6, the extract evaporated, and the residue purified by sublimation to give 2,4,6-trichloro-5-cyanopyrimidine (II), plates, m. 122-3.5°. II (1 g.) was added to a solution of 0.67 g. Na in 30 cc. MeOH, refluxed 4 hrs., filtered, the filtrate concentrated, H2O added, and the whole neutralized with HCl to give 2,4-dimethoxy-5-cyano-6-hydroxypyrimidine (III), needles, m. 217-18° (decomposition) (MeOH). III (0.3 g.) was heated 2 hrs. with 30 cc. 5% KOH solution on a steam bath, acidified with HCl, and the mixture filtered to give 2,4,6-trihydroxy-5-cyanopyrimidine, m. above 360°.

Takamine Kenkyusho Nenpo published new progress about Alcoholysis. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, COA of Formula: C5H6ClN3O.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Okui, Kiyoshi published the artcile< Chemistry of sulfanilamidopyrimidine. Abnormal condensation products of 4-amino-6-chloro-2-methoxypyrimidine with p-nitro-benzenesulfonyl chloride>, Reference of 3286-55-3, the main research area is pyrimidine nitrobenzenesulfonyl chloride reaction; nitrobenzenesulfonamidopyrimidine; pyrimidinium betaine nitrobenzenesulfonamidopyrimidine.

Reaction of 4-amino-6-chloro-2-methoxypyrimidine with 4-ClSO2C6H4NO2 in the presence of pyridine gave the pyridinium betaines I and II in addition to the sulfonamide III. The yield of I increased with reaction time, accompanied by a corresponding decrease in III yield. I was also prepared by heating III with pyridine. The structure of II was also confirmed.

Heterocycles published new progress about 3286-55-3. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, Reference of 3286-55-3.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Khmel’nitskii, R. A.; Klyuev, N. A.; Kunina, E. A.; Kropacheva, A. A. published the artcile< Mass spectra of methoxy derivatives of 4-aminopyrimidines>, Recommanded Product: 6-Chloro-2-methoxypyrimidin-4-amine, the main research area is mass spectra pyrimidinamine.

Mass spectra of the 2-methoxy-6-methyl, 6-methoxy-2-methyl, 2-methoxy-5-methyl, 2,6-dimethoxy, and 6-chloro-2-methoxy derivatives of 4-pyrimidinamine were determined and correlated with structure.

Khimiya Geterotsiklicheskikh Soedinenii published new progress about Mass spectra. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, Recommanded Product: 6-Chloro-2-methoxypyrimidin-4-amine.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Spiteller, G.; Bretschneider, H. published the artcile< Preparation of 2,6-disubstituted 4-sulfanilamidopyrimidines>, Related Products of 3286-55-3, the main research area is .

Crude 2,6-dichloro-4-aminopyrimidine (I) (21.2 g.) was treated portionwise with 50 ml. NaOMe (3.14 g. Na) at 35°, the mixture heated 1 hr. at 50° with stirring, MeOH distilled in vacuo at 40°, and the residue treated with 30 ml. H2O yielded after filtration 14.2 g. 2-methoxy-4-amino-6-chloropyrimidine (II), m. 130° (H2O), sublimable at 120° (0.5 mm.). CaCO3Pd catalyst (1.3 g.) hydrogenated in 10 ml. absolute MeOH was added to 798 mg. II in 35 ml. absolute methanolic NaOH and the mixture hydrogenated to yield 510 mg. 2-methoxy-4-aminopyrimidine, m. 160-7°; mixed m.p. with authentic material gave no depression. II (13.4 g.) was treated with 20 ml. NaOMe (113 mg. Na/ml.) and 10 ml. 90% EtSH, the mixture heated 2 hrs. at 100° in an autoclave, cooled, MeOH and excess EtSH distilled in vacuo, the residue treated with 20 ml. H2O, the oil obtained dissolved in 150 ml. Et2O, washed with H2O, dried, evaporated, and petr. ether added to give 13.1 g. 2-methoxy-4-amino-6-ethylthiopyrimidine (III), m. 83-4°, b0.5 140°. I (24.6 g.) was treated with 20 ml. EtSH, 48 ml. absolute MeOH, and 3.75 g. Na, the mixture heated 1 hr. in an autoclave at 50°, MeOH and excess EtSH distilled in vacuo at 50°, the residue taken up in 20 ml. H2O and 200 ml. Et2O, washed with H2O, the Et2O solution dried, and 2-ethylthio-4-amino-6-chloropyrimidine (IV) precipitated with petr. ether, m. 78-79°, b0.5 130°. Crude IV (17.5 g.) was treated with 30 ml. NaOMe solution (containing 2.1 g. Na) in an autoclave 2 hrs. at 100°, the mixture evaporated, and the residue treated with H2O to give 2-ethylthio-4-amino-6-methoxy pyrimidine (V), m. 117-18° (Et2O), b0.5 135-40°. I (8.4 g.) treated in an autoclave with 20 ml. EtSH and 38 ml. NaOMe (2.8 g. Na) and heated 6 hrs. at 110° gave 2,6-bis(ethylthio)-4-aminopyrimidine (VI), m. 72-3° (petr. ether), b0.5 155-60°. I (8.2 g.) treated with 60 ml. absolute CH2:CHCH2OH and 4 g. Na 2 hrs. at 100° yielded after evaporation in vacuo 2,6-diallyl-4-aminopyrimidine (VII), m. 48-53° (Et2O-petr. ether), b0.5 120-30°. Na (5.5 g.) in 60 ml. HOCH2CH2OMe was heated 3 hrs. at 100° with 16 g. crude I in an autoclave, the mixture evaporated in vacuo, the residue extracted with 500 ml. C6H6, the extract washed neutral with H2O, boiled with active C, filtered, and freed of solvent to give 2,6-bis(β-methoxyethoxy)-4-aminopyrimidine (VIII), m. 84-5° (MeOH-Et2O), and a compound, m. 63-4°. Freshly distilled PhNH2 (92 g.), 150 ml. Et2O, and 100 ml. H2O was treated dropwise with 108 g. ClCO2Et in 50 ml. Et2O at 5°, 54 g. ClCO2Et, then 40 g. NaOH in 60 ml. H2O added by a dropping funnel, the mixture stirred 15 min., the precipitate separated and extracted with Et2O, freed of solvent, and the residue distilled in vacuo to give 90% phenylurethan (IX), b11 145-6°, m. 53° (H2O). To 250 ml. HSO3Cl cooled with an ice-salt mixture was added in 5 g. portions 80 g. IX, the temperature was held at 5° maximum, the mixture stirred 15 min. at 5°, left overnight, heated 1 hr. at 75-80° on a water bath, cooled, poured on ice, the precipitated crystals filtered off, washed with NaHCO3 solution and H2O, extracted in 600 ml. C6H6, and the extract filtered hot gave 46 g. N4-carbethoxysulfanilic chloride (X), m. 103° (C6H6). The aminopyrimidines were converted to compounds of the general formula R3NHC6H4SO2NHC:-N.CR2:N.CR1:CH (Xa) by treatment with 5-10% excess X in 2.5 times absolute C5H5N. The mixture was kept briefly at room temperature, heated 1 hr. at 70-80°, C5H5N evaporated in vacuo, the residue treated with 10% NaHCO3, and the precipitated Na salt dissolved in excess H2O to give, after filtration and acidification of the filtrate, the acylated sulfonamide. V yielded 94% Xa (R1 = EtS, R2 = MeO, R3 = EtOCO) (XI), m. 172-3° (EtOH); III gave 82% Xa (R1 = MeO, R2 = EtS, R3 = EtOCO) (XII), m. 188-9° (EtOH); VI yielded 88% Xa (R1 = R2 = EtS, R3 = EtOCO) (XIII), m. 167-8° (EtOH); VII gave 94% Xa (R1 = R2 = CH2:CHCH2OH, R3 = EtOCO) (XIV), m. 164-5° (EtOH); and VIII yielded 60% Xa (R1 = R2 = MeOCH2CH2O, R3 = MeCO) (XV), m. 164-5° (MeOH). The acylsulfonamides were hydrolyzed by heating 1 hr. in 5 moles N NaOH on a water bath and the cooled solution neutralized by dropwise addition of 50% AcOH to give sulfonamides of the general formula H2NC6H4SO2NHC:N.CR2:N.CR’:CH (XVa). XI yielded 97% XVa (R1 = EtS, R2 = MeO), m. 178-9°; XII gave 75% XVa (R1 = MeO, R2 = EtS), m. 181-2°; XIII gave 94% XVa (R1 = R2 = EtS), m. 176-7°; XIV yielded 90% XVa (R1 = R2 = CH2:CHCH2O), m. 163-4°; and XV gave XVa (R1 = R2 = MeOCH2CH2O) (XVI). XVI was converted to the appropriate Ag salt, m. 262-4° (decomposition). The Ag salt of XVI was treated with H2S and the precipitated Ag2S filtered off, and the solution evaporated in vacuo. The residue was treated with Ac2O in C5H5N 2 days at room temperature and 20 min. on a water bath, freed of solvent, and poured into Na2CO3 solution, filtered, and the filtrate neutralized with AcOH to give XV. The Na salt of XV was not obtained in a pure form.

Monatshefte fuer Chemie published new progress about 3286-55-3. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, Related Products of 3286-55-3.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Nakazawa, Junichi; Watatani, Mitsuo published the artcile< Pyrimidine derivatives. I. Sulfanilamide derivatives>, Product Details of C5H6ClN3O, the main research area is .

4-Sulfanilamido-2,6-disubstituted pyrimidines were prepared A mixture of 3.8 g. 2,6-dihydroxypyrimidine, 38 cc. POCl3, and 9 g. PhNMe2 was refluxed 2 hrs., excess of POCl3 removed, the residue decomposed with ice, the mixture adjusted to pH 2.8, and kept overnight to give 3.9 g. 2,6-dichloro-4-aminopyrimidine (I), needles, m. 270-1° (MeOH). A mixture of 16.3 g. 2-methoxy-4-amino-6-hydroxypyrimidine, 23.6 g. Ac2O, and 23.6 g. AcOH was refluxed 1 hr. to give 19.3 g. 2-methoxy-4-acetamido-6-hydroxypyrimidine (II), m. 275-80° (decomposition). Similarly was prepared 2-ethoxy-4-acetamido-6-hydroxypyrimidine (needles, m. 258-9° (decomposition) (EtOH)). A mixture of II (9 g.) 30.2 POCl3, and 6 g. PhNMe2 was refluxed 1.5 hrs., the excess of POCl3 removed, and the residue decomposed with ice to give 8.6 g. 2-methoxy-4-acetamido-6-chloropyrimidine (III), columns, m. 197-8° (AcOEt). Similarly was prepared 2-ethoxy-4-acetamido-6-chloropyrimidine, columns, m. 193° (C6H6 or AcOEt). III (13 g.) was heated 10 min. with 5.2 g. NaOH and 200 cc. 90% MeOH, the whole neutralized, the MeOH removed, H2O added, and the resulting crystals recrystallized from C6H6 to give 9.1 g. 2-methoxy-4-amino-6-chloropyrimidine (IV), needles, m. 128-9°. Similarly was prepared 2-ethoxy-4-amino-6-chloropyrimidine, needles, m. 128-9° (C6H6). I (1.7 g.) was refluxed 4 hrs. with 1.2 g. NaOH and 12 cc. MeOH, the mixture, filtered, the filtrate concentrated, and H2O added to give 1.5 g. 2,6-dimethoxy-4-aminopyrimidine (V), columns, m. 151-2° (C6H6). Refluxing III or IV with NaOH in MeOH also gave V in 90% yield. Similarly were prepared the following 2,6-RR’ derivatives of 4-aminopyrimidines (R, R’, m.p., and % yield given): OEt, OEt, 107-8°, 95.3; SMe, SMe, 122-3°, 91.6; SEt, SEt, 78-80°, 84; OEt, OMe, 107-8.5°, -; OPh, OMe, 137-8°, 59.9; SMe, OMe, 94-5°, 54.5; SEt, OMe, 78-80°, 52.1; OMe, OEt, 142-3°, 87.6; OEt, SEt, (b1.5 165-9°), 87.3; SPh, OEt, 108.5-9.5°, 70.2. A solution of 4.4 g. V and 7.3 g. 4-acetylsulfanilyl chloride in 14.6 g. C5H5N was kept at room temperature overnight, heated 1 hr. on a steam bath with 73 cc. 10% NaOH solution, H2O added and the mixture evaporated in vacuo, the residue adjusted to pH 4 with HCl, and the resulting crystals recrystallized from MeOH to give 7.8 g. 4-sulfanilamido-2,6-dimethoxypyrimidine, columns, m. 201-2°. Similarly were prepared the following N:C(R).N:C(R’).CH:CNHSO2C6H4NH2-p (data as before): OEt, OEt, 195-6°, 77.8; SMe, SMe, 178-9°, 74.1; SEt, SEt, 178-9°, 79.7; OMe, OEt, -, -; OMe, OPh, 108-10°, 51.4; OMe, SMe, 172-3°, 71.6; OMe, SEt, 175-6°, 73.0; OEt, OMe, 185-6°, 77.9; SEt, OEt, 177-8°, 46.2; OEt, SPh, 206-8°, 61.5.

Takamine Kenkyusho Nenpo published new progress about Alcoholysis. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, Product Details of C5H6ClN3O.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Bretschneider, H.; Kloetzer, W.; Spiteller, G.; Dehler, J. published the artcile< New pyrimidines and their conversion into 6-sulfanilamidopyrimidines. Preliminary communications>, HPLC of Formula: 3286-55-3, the main research area is .

The favorable chemotherapeutic properties of 6-sulfanilamido-2,4-dimethoxypyrimidine (I) motivated the preparation of a number of 2,4-disubstituted 6-sulfanilamidopyrimidines. From II were prepared the following IIa (R, R’, and R” given): MeO, MeO, Cl (III); MeO, MeO, NMe3Cl; MeO, Cl, Cl (IV); MeO, MeO, EtS; MeO, MeO, EtSO2; MeO, MeO, PhS; MeO, MeO, PhSO2; MeO, MeO, 4-AcNHC6H4SO2; Cl, Cl, NH2; MeO, MeO, NH2; EtS, EtS, NH2; CH2:CHCH2O, CH2:CHCH2O, NH2 (V); MeOCH2CH2O, MeOCH2CH2O, NH2; MeO, Cl, NH2; EtS, Cl, NH2; MeO, H, NH2; MeO, EtS, NH2; EtS, MeO, NH2. Also prepared was Va. Two procedures were used to introduce the sulfanilamido group: (1) replacement of the 6-substituent by treatment with 4-H2NC6H4SO2NHNa (VI) or 4-AcNHC6H4SO2NHNa (VII) and (2) the standard acylation with an N4-acylaminobenzenesulfonyl chloride in pyridine followed by hydrolysis. Treatment of II with VII gave (VIII) (R” = Ac, R’ = R = Cl), converted by acid hydrolysis to VIII (R” = H, R’ = R = Cl) (IX). Partial methanolysis of IX with NaOMe gave VIII (R” = H, R’ = Cl, R = OMe) (X) and total methanolysis afforded I. X was also prepared from IV and VII to give VIII (R” = Ac, R’ = Cl, R = OMe) (XI), followed by hydrolysis. Methanolysis of XI followed by hydrolysis gave I. X treated with Me2NH gave VIII (R” = H, R’ = NMe2, R = OMe). I was also obtained from III and VI, and X from IV and VI. V was converted to VIII (R” = Ac, R’ = R = OCH2CH2OMe) and hydrolyzed to VIII (R = H, R’ = R = OCH2CH2OMe). The following VIII (R” = EtO2C) were reported (R and R’ given): MeO, MeO; EtS, EtS; CH2:CHCH2O, CH2:CHCH2O; MeO, EtS; EtS, MeO. Also prepared was XII. Hydrolysis of the above compounds gave the corresponding sulfapyrimidines. Complete details of this work are in preparation

Monatshefte fuer Chemie published new progress about 3286-55-3. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, HPLC of Formula: 3286-55-3.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Okui, Kiyoshi; Ito, Kiyohiko; Koizumi, Masuo; Fukumoto, Keiichiro; Kametani, Tetsuji published the artcile< Syntheses of heterocyclic compounds. CDXCI. Pyrimidine derivatives. V. Abnormal condensation products of 4-amino-6-chloro-2-methoxypyrimidine with p-nitrobenzenesulfonyl chloride>, Related Products of 3286-55-3, the main research area is pyridinium pyrimidine betaines.

Condensation of 4-amino-6-chloro-2-methoxypyrimidine with p-O2NC6H4SO2Cl gave, in addition to 6-chloro-2-methoxy-4-(p-nitrobenzenesulfonamido)pyrimidine (I), two abnormal by-products, 1-[2-methoxy-4-(p-nitrobenzenesulfonamido)pyrimidin-6-yl]pyridinium N,N-betaine (II) and N-(p-nitrobenzenesulfonyl)-β-ureido-β-pyridinium arcylamide N,N-betaine (III).

Journal of Heterocyclic Chemistry published new progress about 3286-55-3. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, Related Products of 3286-55-3.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Nitta, Yoshihiro; Okui, Kiyoshi; Ito, Kiyohiko published the artcile< Pyrimidine derivatives. I. Synthesis of a new series of sulfanilamides having dialkylamino groups in the pyrimidine nucleus>, Name: 6-Chloro-2-methoxypyrimidin-4-amine, the main research area is .

A solution of 7.1 g. Na in 300 mL. ROH was added dropwise to 50 g. 4-amino-2,6-dichloropyrimidine (I) in 3 l. of ROH during 6 h. at 50-60°. After 20 h. ROH was removed, mixture washed with H2O and crystallized to give II (R1 = Cl) (R, m.p., % yield, crystallization solvent given): MeO, 127-8°, 72, H2O; EtO, 128-9°, 75, MeOH-H2O; PrO, 114-15°, 78, MeOH-H2O; iso-Pr, 134-5°, 72, MeOH-H2O. The Cl compounds heated at 120° for 4-6 h. in a sealed tube with 20% Me2NH/MeOH gave II (R1 = NMe2) (R, m.p., % yield, crystn solvent given): MeO, 158-9°, 85, H2O; EtO, 136-7°, 95, C6H6; PrO, 96-7°, 87, ligroine; iso-Pr, 105-6°, 82, ligroine. II (R = Cl, R1 = MeO) (IIa) (16 g.) heated on the steam bath 2 h. in 200 mL. 10% NaOH and acidified with AcOH (pH 6) gave 12 g. 4-amino-6-chloro-2(1H)-pyrimidone (III), m. >300° (H2O). IIa treated with Me2NH as above and treated with NaOH gave 4-amino-6-dimethylamino-2(1H)-pyrimidone (IV), m. >300° (H2O). III and Me2N also gave IV. I (60 g.) in 300 mL. of 20% R3R2NH/MeOH became clear after stirring sometimes with heat for 4 h. Concentration and crystallization gave II (R = Cl) (R1, m.p., % yield, crystallization solvent given): Me2N, 152-3°, 73, H2O; Et2N, 124-5°, 75, C6H6; (CH2)4N, 184-5°, 90, MeOH-H2O; morpho-linoe, 153-4°, 84, MeOH-H2O; (H2C:CHCH2)2N, 91-3° (acetyl derivative), –, ligroine. Na(7.1 g.)in 3 mL. MeOH added to 50 g. I in 2.5 l. MeOH during 6 h. at 50-60°, the solution concentrated after 20 h. to 300 mL. and diluted with 700 mL. hot H2O gave IIa. The filtrate chilled to -10° gave a mixture which washed with MeOH and crystallized from MeOH gave II (R = MeO, R1 = Cl) (IIb), 3.5 g., m. 187-8°. IIb (0.01 mol) in 100 mL. 1% NH3/MeOH hydrogenated over 0.2 g. 10% Pd/C gave II (R = MeO, R1 = H), m. 155-6° (C6H6). Prepared similarly were II (R1 = H) (R, m.p., % yield given): EtO, 151-2°, 86; PrO, 132-3°, 90; iso-PrO, 93-4°, 92; BuO, 126-7°, 85; iso-BuO, 132-4°, 75; tert-BuO, 66-7°, 75. Similarly, from the 2-alkoxy-4-amino-6-chloropyrimidines were prepared II (R = H) (R1, m.p., % yield, crystallization solvent given): MeO, 168-9°, 75, H2O; EtO, 83-6°, 86, ligroine; PrO, 77-8°, 86, ligroine; iso-PrO, 75-6°, 85, ligroine. II (R and R1 = alkoxy) were obtained from II (R = XO, R1 = Cl) with NaOH and an alc. (R, R1, m.p., % yield, all crystallized from MeOH-H2O): MeO, MeO, 150-1°, 96; MeO, EtO, 144-5°, 94; MeO, iso-PrO, 98-9°, 91; EtO, MeO, 112-13°, 95. II (R = XO, R1 = Cl) and NaSR in the corresponding alcs. heated 3 h. on the steam bath, diluted with H2O and the product crystallized from dilute MeOH gave II (R, R1, m.p., % yield given): MeO, MeS, 143-4°, 94; MeO, EtS, 116-17°, 83; MeO, PrS, 99-100°, 80; MeO, iso-PrS, 116-17°, 86; EtO, MeS, 92-3°, 93; EtO, iso-PrS, 74-5°, 95. II (R = XO, R1 = Cl) (0.01 mol) in 200 mL. 10% Me2NH/MeOH heated at 100° 5 h. in a sealed tube gave II (R, R1, m.p., % yield, crystallization solvent given): MeO, Me2N, 93-4°, 95, ligroine; EtO, Me2N, 86-7°, 87, MeOH-H2O; H, Me2N, 153-5°, 90, C6H6. I (30 g.) in 200 mL. 20% Me2NH/MeOH heated at 120-130° for 6 h. in a sealed tube, concentrated, and diluted with 100 mL. of 10% NaOH gave 25 g. II (R = R1 = NMe2), m. 116-17° (H2O). Acetyl derivatives of the following II were prepared and crystallized from MeOH or dilute MeOH (R, R1, m.p., yield % given): Cl, MeO, 195-6°, 94; Cl, EtO, 194-6°, 94; MeO, Cl, 216-17°, 93; EtO, Cl, 215-16°, 90; MeO, H, 138-9°, 94; EtO, H, 130-1°, 95; PrO, H, 135-6°, 74; iso-PrO, H, 105-6°, 70; BuO, H, 95-6°, 63; MeO, Me2N, 187-8°, 90; EtO, Me2N, 166-7°, 92; PrO, Me2N, 165-7°, 84; iso-PrO, Me2N, 156-7°, 87; EtS, Me2N, 155-6°, 83; PrS, Me2N, 165-7°, 94; iso-PrS, Me2N, 186-7°, 90. The 4-aminopyrimidines and p-MeCONHC6H4SO2Cl in C5H5N (1 mL./g. chloride) at room temperature 12 h. were diluted with H2O and the crude products (V) (R2 = Ac) hydrolyzed in 10 volumes of 10% NaOH at 100° for 1 h. and neutralized with AcOH to give V (R2 = H). V (R2 = Ac) (R, R1, m.p., % yield, crystallization solvent given): Me2N, MeO, 218-20°, 82, MeOH; Me2N, EtO, 220-4°, 74, MeOH; Me2N, PrO, 215-16°, 70, MeOH; Me2N, iso-PrO, 166-7°, 74, MeOH; MeO, Me2N, 251-3°, 69, MeOH; EtO, Me2N, 223-4°, 75, MeOH; PrO, Me2N, 161-2°, 73, MeOH; EtS, Me2N, 226-7°, 81, MeOH-H2O; PrS, Me2N, 203-5°, 75, MeOH-H2O; iso-PrS, Me2N, 180-2°, 86, MeOH-H2O; Cl, Me2N, 261-2°, 70, MeOH; Cl, Et2N, 194-5°, 50, MeOH; Cl, (C3H6)2N, 178-9°, 29, MeOH-H2O; Cl, (CH2)4N, 234-5°, 81, MeOH-H2O; Cl, morpholino, 273-4°, 75, Me2CO; Me2N, H, 296-7°, 72, MeOH; Me2N, Me2N, 210-15° (crude), 32, –; Me2N, MeS, 230-5° (crude), 85, –. V (R2 = H, given as above): Me2N, MeO, 207-8°, 95, MeOH; Me2N, EtO, 228-30°, 87, MeOH-H2O; Me2N, PrO, 182-3°, 92, MeOH-H2O; Me2N, iso-PrO, –, 92, MeOH-H2O; MeO, Me2N, 218-20°, 90, MeOH-H2O; EtO, Me2N, 185-6°, 90, MeOH-H2O; PrO, Me2N, 90-1°, 65, Me2CO-C6H6; EtS, Me2N, 139-40°, 87, MeOH-H2O; PrS, Me2N, 165-7°, 70, MeOH-H2O; iso-PrS, Me2N, 170-1°, 76, MeOH-H2O; Cl, Me2N, 203-4°, 92, Me2CO-H2O; Cl, Et2N, 178-80°, 93, MeOH-H2O; Cl, (C3H5)2N, 170-2°, 98, MeOH-H2O; Cl, (CH2)4N, 234-5°, 84, Me2CO-H2O; Cl, morpholino, 280-2°, 89, Me2CO-H2O; Me2N, H, 276-7°, 64, MeOH; Me2N, Me2N, 221-3°, 56, MeOH; Me2N, MeS, 242-3°, 68, MeOH-H2O. V (R = R2 = H, R1 = Me2N), m. 146-7° (MeOH-H2O), was prepared in 82% yield from V (R = Cl, R1 = Me2N, R2 = H). V (R = MeO, R1 = Et2N, R2 = H), m. 186-8° (MeOH-H2O), was prepared in 85% yield from V (R = Cl, R1 = Et2N, R2 = H). V (R = Cl, R1 = NR3R4, R2 = H) showed good antibacterial properties.

Chemical & Pharmaceutical Bulletin published new progress about 3286-55-3. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, Name: 6-Chloro-2-methoxypyrimidin-4-amine.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3286-55-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.3286-55-3, name is 6-Chloro-2-methoxypyrimidin-4-amine, molecular formula is C5H6ClN3O, molecular weight is 159.57, as common compound, the synthetic route is as follows.

Step 1: 4-(6-amino-2-methoxypyrimidin-4-yl)benzonitrile To a mixture of 6-chloro-2-methoxypyrimidin-4-amine (Ark Pharm, catNo.AK-25131: 1.3 g, 8.0 mmol), (4-cyanophenyl)boronic acid (1.41 g, 9.60 mmol) and sodium carbonate (1.7 g, 16 mmol) in 1,4-dioxane (15 mL) and water (5 mL) was added dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (170 mg, 0.24 mmol). The reaction mixture was purged with nitrogen then stirred at 95 C. overnight. The reaction mixture was cooled to room temperature then water (20 mL) was added. The resulting precipitate was collected via filtration then dried to give the desired product (1.7 g, 94%), which was used in the next step without further purification. LC-MS calculated for C12H11N4O (M+H)+: m/z=227.1. found 227.1.

Statistics shows that 3286-55-3 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-2-methoxypyrimidin-4-amine.

Reference:
Patent; Incyte Corporation; He, Chunhong; Li, Zhenwu; Wu, Liangxing; Yao, Wenqing; Zhang, Fenglei; (84 pag.)US2016/289238; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia