In 1965,Chemical & Pharmaceutical Bulletin included an article by Nitta, Yoshihiro; Okui, Kiyoshi; Ito, Kiyohiko. Product Details of 3286-56-4. The article was titled 《Pyrimidine derivatives. I. Synthesis of a new series of sulfanilamides having dialkylamino groups in the pyrimidine nucleus》. The information in the text is summarized as follows:
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. After reading the article, we found that the author used 6-Chloro-2-ethoxypyrimidin-4-amine(cas: 3286-56-4Product Details of 3286-56-4)
6-Chloro-2-ethoxypyrimidin-4-amine(cas: 3286-56-4) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.Product Details of 3286-56-4
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia