31058-83-0 | Pyrimidines

Share a compound : 6-Chloro-N,N-dimethylpyrimidin-4-amine

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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. 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine. A new synthetic method of this compound is introduced below., Computed Properties of C6H8ClN3

To a solution of N- (cis-4-amino-cyclohexyl)-3, 4-difluoro-benzamide (442 mg) was added (6-chloro-pyrimidin-4-yl)-dimethyl-amine obtained in step A of example 1 (250 mg). The mixture was stirred at 180C for 8 hr in a sealed tube. To the mixture was added saturated aqueous NaHC03 and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (NH-silica gel, 33% to 50% EtOAc in hexane and silica gel, 3% MeOH in CHCI3) to give N-(cis-4-{[6- (dimethylamino) pyrimidin-4-yl] amino} cyclohexyl)-3, 4-difluorobenzamide. To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried at 70C under reduced pressure to give N-(cis-4-{[6- (dimethylamino) pyrimidin-4-yl] amino} cyclohexyl)-3, 4-difluorobenzamide hydrochloride (99 mg). ESI MS m/e 398, M (free) +Na+ ;’H NMR (300 MHz, CDCI3) 8 1.69-2. 15 (m, 8 H), 3.00- 3.42 (m, 6 H), 3.69-3. 81 (m, 1 H), 4.03-4. 21 (m, 1 H), 5.26 (s, 1 H), 6.66-6. 80 (m, 1 H), 7.13-7. 26 (m, 1 H), 7.51-7. 62 (m, 1 H), 7.68-7. 80 (m, 1 H), 8.01 (s, 1 H), 8.68-8. 91 (m, 1 H), 13.84-14. 09 (m, 1 H).

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Extended knowledge of 6-Chloro-N,N-dimethylpyrimidin-4-amine

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. 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 31058-83-0

Example 33: N.N-Dimethyl-e-KIS.eRVe-tP-iS-methyl-l ^^-oxadiazol-S- l)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]oct-3-yl]pyrimidin-4-amine.A mixture of Intermediate 12 (50 mg, 0.17 mmol), 2-chloro-4,6- dimethylpyrimidine (24 mg, 0.17 mmol) and DIPEA (0.87 mL, 0.5 mmol) in ACN (1 mL) was heated in the microwave at 200 C for 2 h. The mixture was concentrated in vacuo and chromatography (Hex to 100% EtOAc/Hex) to afford the desired product as a pale yellow foam (39 mg, 55%). MS (ESI) mass calculated for C22H25N7O2, 419.2; m/z found, 420.2. 1 H NMR (500 MHz, CDCI3): 8.15 (s, 1 H), 8.12 – 8.04 (m, 1 H), 7.59 – 7.50 (m, 2H), 7.25 – 7.17 (m, 1 H), 5.22 (s, 1 H), 4.44 – 4.33 (m, 2H), 4.1 1 – 3.99 (m, 1 H), 3.94 – 3.73 (m, 2H), 3.68 – 3.60 (m, 1 H), 3.1 1 – 3.05 (m, 6H), 3.02 – 2.86 (m, 2H), 2.45 – 2.42 (m, 3H), 2.22 – 1 .97 (m, 2H).

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Analyzing the synthesis route of 31058-83-0

The synthetic route of 31058-83-0 has been constantly updated, and we look forward to future research findings.

Electric Literature of 31058-83-0 , The common heterocyclic compound, 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine, molecular formula is C6H8ClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A mixture ofN-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine (466 mg), (6-chloro-pyrimidin-4-yl) -dimethyl-amine (200 mg), and ethylene glycol (0.5 mL) was stirred at reflux for 4 hr in a sealed tube. The mixture was poured into saturated aqueous NaHC03 and the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane and silica gel, 501-‘o MeOH in CHCl3) to give N’- (cis-4- { [4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N, N-dimethylpyrimidine-4, 6-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N’-(cis-4-{[4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N,N-dimethylpyrimidine-4, 6-diamine dihydrochloride (67 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDC13) 8 1.64-1. 86 (m, 2 H), 1.96- 2.34 (m, 8 H), 2. 98-3.44 (m, 8 H), 4.27 (s, 2 H), 7.40-7. 59 (m, 3 H), 8.06-8. 24 (m, 2 H).

The synthetic route of 31058-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia