Water → 3-methyl-2-(2-oxo-2-phenylethylamino)-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 32302Notes

Reaction equation

HRID 32302 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl[C:13]1[N:18]([CH3:19])[C:17](=[O:20])[CH:16]=[C:15]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:14]=1.C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.CS(C)=O>[CH3:19][N:18]1[C:17](=[O:20])[CH:16]=[C:15]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:14]=[C:13]1[NH:2][CH2:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-

Product 1

HCID 103085893-methyl-2-(2-oxo-2-phenylethylamino)-6-pyridin-4-yl-3H-pyrimidin-4-oneYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-amino-1-phenyl-ethanone hydrochloride (1.03 g, 6.00 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (0.665 g, 3.00 mmol), 4-dimethylaminopiridine (36.0 mg, 0.30 mmol) and triethylamine (0.80 ml, 6.00 mmol) in dimethylsulfoxide (15 ml) was stirred at room temperature. After stirring for several hours, water was added to the reaction mixture. The precipitate was filtered and washed with refluxing diethyl ether to give the title compound (0.556 g, 68%).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with refluxing diethyl ether

Sources & evidence

ORD record
ord-618c8222f17d4da58701e421bc67217f
Source dataset
uspto-grants-2008_09
Patent number
US07427615B2

Reaction notes

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