Triethylamine → 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][O:6][C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH2:30].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][O:6][C:7]1[C:12]([C:13]([NH:30][CH2:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)=[O:15])=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic acid (300 mg, 0.88 mmol) and pyridin-2-ylmethylamine (115 mg, 1.06 mmol) were dissolved in 10 mL of THF, triethylamine (141 mg, 1.4 mmol) was added dropwise, added HATU (405 mg, 1.06 mmol) under ice-water-bath, reacted at room temperature for 4 h, to the reaction solution was added 100 mL of water, then extracted with dichloromethane, dried with anhydrous sodium sulfate, dried by rotation, then the solid was separated with silica gel column (dichloromethane:methanol=20:1) to obtain a white solid 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide 180 mg, yield 48%.
Workup
- customreacted at room temperature for 4 h, to the reaction solution
- extractionextracted with dichloromethane
- dry with materialdried with anhydrous sodium sulfate
- customdried by rotation
- customthe solid was separated with silica gel column (dichloromethane:methanol=20:1)
Sources & evidence
- ORD record
- ord-a4b3b7ee9b164790a50d38ef128e0ced
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08980904B2
Reaction notes
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