Triethylamine → (S)-4-(4-(1,6-dihydro-1-methyl-6-oxo-4-(pyrimidin-4-yl)pyrimidin-2-yl)-[1,4]oxazepan-6-yl)benzonitrile

Reaction equation

Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[N:3]=1.[O:16]1[CH2:22][C@@H:21]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C>>[CH3:8][N:7]1[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[N:3]=[C:2]1[N:19]1[CH2:20][C@H:21]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH2:22][O:16][CH2:17][CH2:18]1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

HCID 67281424(S)-4-([1,4]oxazepan-6-yl)benzonitrile

Product 1

HCID 46935963(S)-4-(4-(1,6-dihydro-1-methyl-6-oxo-4-(pyrimidin-4-yl)pyrimidin-2-yl)-[1,4]oxazepan-6-yl)benzonitrileYield 73.2%

Procedure

To a solution of 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (73.4 mg, 0.330 mmol) and (S)-4-([1,4]oxazepan-6-yl)benzonitrile (70.0 mg, 0.346 mmol) was added triethylamine (100 mg, 0.989 mmol) at room temperature. The mixture was stirred at room temperature for 5 hours and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/9) to afford (S)-4-(4-(1,6-dihydro-1-methyl-6-oxo-4-(pyrimidin-4-yl)pyrimidin-2-yl)-[1,4]oxazepan-6-yl)benzonitrile (A076) as white solid (93.8 mg, 70%).