Day: September 16, 2021

Adding a certain compound to certain chemical reactions, such as: 116247-92-8, 1-Pyrimidin-2-yl-piperidin-4-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C9H11N3O, blongs to pyrimidines compound. Computed Properties of C9H11N3O

To a solution of LDA (prepared from diisopropylamine (167.4 mg, 1.658 mmol) and n-BuLi (2.5 M in hexanes, 0.663 ml, 1.658 mmol) at -78 C., was added a solution of the above 1-pyrimidin-2-yl-piperidin-4-one (320 mg, 1.382 mmol). The mixture was stirred at the same temperature for 1 hour, followed by the addition of PhNTf2 (543.1 mg, 1.52 mmol). The reaction mixture was warmed up to room temperature and stirred for 3 hours before it was quenched with the addition of saturated ammonium chloride (15 ml) and EtOAc (40 ml). After separation of the layers, the aqueous phase was extracted with EtOAc (2*10 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (20% EtOAc/hexanes) to give the corresponding triflate (210.7 mg, 49%) as a white solid as long with recovered starting material (142.9 mg): 1H NMR (CDCl3, 400 MHz) delta 8.37 (d, J=6.4 Hz, 2 H), 6.59 (t, J=6.4 Hz, 1 H), 5.91 (m, 1 H), 4.41 (m, 2 H), 4.11 (t, J=5.6 Hz, 2 H), 2.55 (m, 2 H); MS calc’d for C10H11F3N3O3S [M+H]+: 310; Found: 310.

The synthetic route of 116247-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barbosa, Joseph; Dong, Li; Fink, Cynthia Anne; Wang, Jiancheng; Zipp, G. Gregory; US2006/258672; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5177-27-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloropyrimidin-5-amine (1.89 g, 11.52 mmol), DIPEA (8.05 ml, 46.1 mmol), morpholine-3-carboxylic acid (1.66 g, 12.68 mmol), and DMSO (5 ml). The reaction was stirred at 100 C. overnight. The reaction mixture was poured into water and extracted with EtOAc 3 times. The pH of the aqueous layer was adjusted (about 5) with 10% citric acid and extracted again with EtOAc. The combined organic layer dried over MgSO4, filtered, and concentrated in vacuo to furnish a tan solid. The solid was triturated in diethyl ether containing a small amount of EtOH, filtered, and dried to give 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one: 1.95 g (70.3%). MS [M+H] found 241.

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2011/53921; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2557-79-1, 6-Methyl-2-(trifluoromethyl)pyrimidin-4(3H)-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 2557-79-1, blongs to pyrimidines compound. Product Details of 2557-79-1

EXAMPLE VI O,O-Diethyl O-(6-methyl-2-(trifluoromethyl)-4-pyrimidinyl)phosphate STR9 A mixture of 3.6 g of 6-methyl-2-(trifluoromethyl)-4-pyrimidinol, 5.0 g of finely powdered potassium carbonate, 40 ml of acetonitrile and 3.45 g of O,O-diethyl chlorophosphate was stirred and heated under reflux for one hour. At this time, no more of the starting phosphorus compound could be detected by glc. The salts were removed by filtration and the filtrate concentrated under reduced pressure. The residue was taken up in ether, the ether solution washed twice with 5 percent aqueous sodium hydroxide solution, once with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The ether was removed in a rotary evaporator leaving 4.0 g of the above-indicated product as an amber colored oil having a refractive index of nd25 =1.4327. The IR and NMR spectra were in agreement with the desired structure. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 38.41, 4.57 and 9.11 percent, respectively, as compared with the theoretical contents of 38.22, 4.49 and 8.92 percent, respectively, as calculated for the above-named structure (Compound 6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2557-79-1, its application will become more common.

Reference:
Patent; The Dow Chemical Company; US4575499; (1986); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 955368-90-8, 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, blongs to pyrimidines compound. Safety of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

I1 (182.89 mg, 822.85 mumol) and 57-1 (200 mg, 822.85 mumol) were added into 1,4-dioxane (5.00 mL), followed by adding cuprous iodide (156.71 mg, 822.85 mumol), potassium carbonate (159.22 mg, 1.15 mmol) and N,N’-dimethylethylenediamine (79.79 mg, 905.14 mumol, 98.87 muL), the temperature was raised to 95C under nitrogen atmosphere, then reacted for 16 h. Ammonia (20 mL) was added into the reacted mixture, then extracted by EA (3×10 mL), the organic phase was washed by saturated brine (20 mL), dried over anhydrous sodium sulfate, the filtrate was concentrated to give the crude product, which was separated by an automatic column machine COMBI-FLASH (PE/EA=10/1-1/1) to give 57-2. MS m/z: 384.41 [M+H]+

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1780-26-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Compound 32a is prepared according to the procedure described in US/2006/0004067A1 (Bang-Chi Chen, et al, published Jan. 05, 2006).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1780-26-3, 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/219370; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H4ClN3O

Methyl (2-(methylamino)ethyl)carbamic acid tert-butyl ester (1.88 g, 9.99 mmol), 2-chloropyrimidine-4-carboxamide (1.73 g, 10.98 mmol) and potassium carbonate under nitrogen. (1.52g, 10.98mmol) was added toN,N-dimethylformamide (15 mL).The reaction mixture was warmed to 130 C, stirred for 20 hr then cooled to room temperature, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to afford the title compound as a white solid (2.50g, 81.0%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 22536-66-9, 2-Chloropyrimidine-4-carboxamide.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Xianjie; Zhang Yingjun; Zheng Changchun; (42 pag.)CN105085491; (2019); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2227-98-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below.

[0065] (4S)-4-{[l-(Triphenylmethyl)-lH-imidazol-4-yl]methyl}-l,3-oxazolidin-2-one or (4S)-4-{[l-(triphenylmethyl)-lH-imidazol-5-yl]methyl}-l,3-oxazolidin-2-one (P.l). A modified literature procedure [Madrigal, et al.14] was followed. (5)-Histidinol dihydrochloride (0.500 g, 2.34 mmol) and diethyl carbonate (2.86 mL, 23.61 mmol) were stirred together in ethanol (24 mL), then sodium methoxide in methanol solution (25%, 1.6 mL, 7.0 mmol) added. The mixture was heated under reflux for 72 h then the solvent was evaporated and the residue chromatographed on silica gel (CHCl3-MeOH-28% aq. NH4OH, 9: 1:0.1) to give (45)-4-(lH-imidazol-4-ylmethyl)-l,3-oxazolidin-2-one as a colourless solid (0.26 g, 1.56 mmol, 90 – 95% pure). XH NMR (500 MHz, CD3OD): delta 7.61 (d, J = 1.0 Hz, 1H), 6.93 (s, 1H), 4.45-4.40 (m, 1H), 4.18-4.12 (m, 2H), 2.86 (dd, J= 14.7, 4.8 Hz, 1H), 2.80 (dd, J= 14.8, 6.1 Hz, 1H). It was dissolved in DMF (4 mL) then triethylamine (0.42 mL, 3.00 mmol) and trityl chloride (0.489 g, 1.70 mmol) were added. The mixture was stirred for 60 h at rt then diluted with Et20 (60 mL) and the mixture washed with H20 (4 x 5mL), brine (5 mL), dried and the solvent evaporated. The residue was chromatographed on silica gel (gradient of 0 – 5% MeOH in EtOAc) to give P.l as a colourless foam (0.520 g, 54%). XH NMR (500 MHz, CD3OD): delta 7.41 (d, J = 1.4 Hz, 1H), 7.39-7.34 (m, 9H), 7.16-7.1 1 (m, 6H), 6.82 (m, 1H), 4.39 (t, J = 8.4 Hz, 1H), 4.19-4.11 (m, 2H), 2.78 (dd, J = 14.6, 4.9 Hz, 1H), 2.73 (dd, J = 14.6, 6.1 Hz, 1H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 162.1 (C), 143.6 (C x 3), 139.8 (CH), 136.6 (C), 130.9 (CH), 129.32 (CH), 129.27 (CH), 121.6 (CH), 76.9 (C), 70.4 (CH2), 53.4 (CH), 33.9 (CH2). ESI-HRMS calcd for C26H23N3Na02+, (M+Na)+, 432.1683, found 432.1677. [0066] (2S)-2-Amino-3-[l-(triphenylmethyl)-lH-imidazol-4-yl]propan-l-ol or (2S)-2- amino-3-[l-(triphenylmethyl)-lH-imidazol-5-yl]propan-l-ol (P.2). Compound P.l (0.510 g, (0109) I .25 mmol) was dissolved in 2-propanol (7 mL) and potassium hydroxide (2 M, 3 mL, 6 mmol) added. The mixture was heated at 80 C for 6 h then silica gel was added to absorb all the solvent then the solvent was evaporated and the residue chromatographed on silica gel (CHCl3-MeOH-28% aq. NH4OH, 9: 1 :0.1) to give P.2 as a colourless gum (0.478 g, 100%). XH NMR (500 MHz, CD3OD): delta 7.40 (d, J = 1.4 Hz, 1H), 7.38-7.34 (m, 9H), 7.18-7.13 (m, 6H), 6.75 (m, 1H), 3.52 (dd, J= 10.9, 4.5 Hz, 1H), 3.35 (dd, J = 10.9. 6.8 Hz, 1H), 3.09-3.03 (m, 1H), 2.65 (dd, J = 14.4, 6.0 Hz, 1H), 2.50 (dd, J = 14.4, 7.4 Hz, 1H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 143.7 (C), 139.7 (CH), 139.2 (C), 130.8 (CH), 129.3 (CH), 129.2 (CH), 121.0 (CH), 76.8 (C), 66.7 (CH2), 53.8 (CH), 33.0 (CH2). ESI-HRMS calcd for C25H26N30+, (M+H)+, 384.2071, found 384.2068. [0067] (2S)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3-[l- (triphenylmethyl)-lH-imidazol-4-yl]propan-l-ol or (2S)-2-[({4-amino-5H-pyrrolo[3,2- d]pyrimidin-7-yl} methyl)amino] -3 – [ 1 -(triphenylmethyl)- 1 H-imidazol-5-yl]propan- 1 -ol (P.3). Compound P.2 (0.200 g, 0.52 mmol), 9-deazaadenine (0.070 g, 0.52 mmol) and aq. formaldehyde solution (37%, 0.051 mL, 0.68 mmol) were heated at 70 C in tert-butanol (3 mL) forl6 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue chromatographed on silica gel (10% 7M NH3/MeOH-CHCl3) to give P.3 as a colourless foam (0.101 g, 37%). XH NMR (500 MHz, CD3OD): delta 8.03 (s, 1H), 7.39 (s, 1H), 7.35 (d, J = 1.3 Hz, 1H), 7.33-7.29 (m, 9H), 7.12-7.08 (m, 6H), 6.75 (d, J = 1.2 Hz, 1H), 3.96 (d, J = 13.7 Hz, 1H), 3.93 (d, J = 13.6 Hz, 1H), 3.61 (dd, J = 1 1.3, 4.8 Hz, 1H), 3.49 (dd, J = (0111) I I.3, 6.1 Hz, 1H), 3.02-2.97 (m, 1H), 2.72 (dd, J = 14.5, 6.5 Hz, 1H), 2.69 (dd, J = 14.5, 6.7 Hz, 1H). C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.0 (C), 150.8 (CH), 146.6 (C), 143.7 (C x 3), 139.5 (CH), 139.2 (C), 130.8 (CH), 129.24 (CH), 129.20 (CH), 128.9 (CH), 121.2 (CH), 115.4 (C), 114,8 (C), 76.8 (C), 64.3 (CH2), 59.4 (CH), 41.3 (CH2), 30.7 (CH2). ESI-HRMS calcd for C32H32 70+, (M+H)+, 530.2663, found 530.2666. [0068] (2S)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3-(lH- imidazol-4-yl)propan-l-ol (PA). Trifluoroacetic acid (0.6 mL, 8 mmol) was added to a stirred solution of P.3 (0.100 g, 0.19 mmol) and triethylsilane (0.090 mL, 0.57 mmol) in CH2CI2 (3 mL). After 2 h, the solvent was evaporated and the residue dissolved in MeOH and the solvent evaporated (3 x). The residue was again dissolved in MeOH, silica gel added and the solvent evaporated. Flash chromatography on silica gel (CHCl3-MeOH-28% aq. NH4OH, 7:2.5:0.5) gave P.4 as a colourless gum which crystallized on standing (0.050 g, 92%). XH NMR (500 MHz, CD3OD): delta 8.14 (s, 1H), 7.52 (d, J= 0.9 Hz, 1H), 7.42 (s, 1H), 6.80 (s, 1H), 4.01 (d, J= 13.6 Hz, 1H), 3.98 (d, J= 13.6 Hz, 1H), 3.63 (dd, J= 11.3, 4.7 Hz, 1H), 3.50 (dd, (0113) J = 11.3, 5…

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2227-98-7, 4-Aminopyrrolo[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; SCHRAMM, Vern, L.; CLINCH, Keith; GULAB, Shivali, Ashwin; WO2015/123101; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4Cl2N2

To a solution OF 4-HYDROXY-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (6.26 g, 33.4 mmol) and 4,6-dichloro-5-methyl-pyrimidine (5.45 g, 33.4 mmol) in 100 mL THF, 1M potassium TERT- butoxide in THF (40 mL, 40 mmol) were added slowly by syringe pump. After 1 hour, everything had been added and mixture was concentrated. Residue was extracted with methylene chloride and water. Organic phases were dried over magnesium sulfate, filtered, and concentrated to give 4- (6- CHLORO-5-METHYL-PYRIMIDIN-4-YLOXY)-PIPERIDINE-1-CARBOXYLIC acid isopropyl’ester as a pale yellow solid (10.3 g, 98%). H NMR (CDC13, 400 MHz) 8 1.22-1. 24 (d, 6H), 1.74-1. 81 (M, 2H), 1.95-2. 04 (M, 2H), 2.24 (s, 3H), 3.40-3. 45 (M, 2H), 3.74-3. 81 (M, 2H), 4.90-4. 98 (M, 1H), 5.31-5. 37 (M, 1H), 8.40 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-97-6, 4,6-Dichloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5018-38-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine, molecular formula is C5H4Cl2N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 3.4 Preparation of 4-(6-Chloro-5-methoxy-pyrimidin-4-yloxy)-piperidine-1-carboxylic Acid Isopropyl Ester A solution of 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (71.0 g, 380 mmol) and 4,6-dichloro-5-methoxypyrimidine (71.6 g, 400 mmol) in anhydrous THF (1 L) was cooled to 5 C. under N2. A solution of potassium t-butoxide (1.0 M in THF, 380 mL, 380 mmol) was added dropwise over 1 h. The reaction temperature was kept under 10 C. during addition. The reaction mixture was stirred at 5-10 C. for 1 h, quenched with saturated NH4Cl (200 mL), and diluted with ether (1 L) and water (1 L). The aqueous phase was separated and discarded. The organic extract was washed with brine (800 mL), dried over MgSO4, and then concentrated. The residue was dissolved in hexane (400 mL) and filtered over Celite to remove a small amount of brown solid. The solvent was removed from the filtrate to afford a pale amber oil which gradually crystallized to give the title compound (130 g, 98.6% yield) as a pale amber solid. Exact Mass calculated for C14H20ClN3O4: 329.1. Found: LCMS m/z=330.2 (M+H+); 1H NMR (400 MHz, CDCl3) delta 1.25 (d, J=6.2 Hz, 6H), 1.82 (m, 2H), 2.02 (m, 2H), 3.40 (m, 2H), 3.80 (m, 2H), 3.91 (s, 3H), 4.95 (m, 1H), 5.39 (m, 1H), 8.27 (s, 1H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5018-38-2, 4,6-Dichloro-5-methoxypyrimidine.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; US2009/286816; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, molecular weight is 154.5571, as common compound, the synthetic route is as follows.Quality Control of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 4-chloro-lH-pyrazolo[3,4-^pyrimidine (J. Amer. Chem. SQC. 1957, 79, 6407-6413) (51 mg, 0.33 mmol) in ethanol (2 ml) was added triethylamine (100 mul, 0.72 mmol) and 4-(N-Boc-aminomethyl)piperidine (87 mg, 0.41 mmol). The solution was heated at 80 C for 3 hours, and then cooled to room temperature. The solution was evaporated to dryness and the residue purified by recrystallisation (isopropanol) to yield the intermediate NH-BOC protected product (33 mg, 30% yield).To the intermediate NH-BOC protected product (32 mg, 0.096 mmol) was added HCl (1 ml, 4M solution in dioxane, 4 mmol). The suspension was stirred at room temperature for 1 hour, and then diluted with diethyl ether (4 ml). The ethereal layer was discarded and the solid washed with a further portion of diethyl ether (2 ml). The ethereal layer was again discarded, and the resultant solid dried under high vacuum. The free base was liberated by dissolution of this material in methanol, loading onto an acidic resin SCX-2 cartridge, and elution from the cartridge with ammonia in methanol to give the title compound (21 mg, quantitative). LC/MS Rt 0.86 [M+H]+233

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2006/46023; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia