Water → HCID 21091746, compound

HRID 271310Notes

Reaction equation

[C@H:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:9]([CH3:21])[C:10](=[O:20])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][N:15]=2)[N:13]=1.[H-].[Na+].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O>[C:24]([N:5]1[CH2:6][C@@H:1]2[CH2:7][CH:4]1[CH2:3][N:2]2[C:8]1[N:9]([CH3:21])[C:10](=[O:20])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][N:15]=2)[N:13]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.13 g (0.46 mmol) of (1S)-2-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-methyl-1H-[4,4′]bipyrimidinyl-6-one in 3 ml of anhydrous dimethylformamide was added 24 mg (0.6 mmol) of sodium hydride and the resulting mixture was stirred at 0° C. for 15 min. There is added 0.07 ml (0.6 mmol) of benzoyl chloride and the resulting solution was stirred at 0° C. for 2h. Water was added to the mixture and the resulting solution extracted with ethyl acetate. The combined extracts were washed with saturated aqueous ammonium chloride and evaporated. The crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 100/0 to 97/3 to give 90 mg (50%) of pure compound as a solid.

Workup

stirringthe resulting solution was stirred at 0° C. for 2h
extractionthe resulting solution extracted with ethyl acetate
washThe combined extracts were washed with saturated aqueous ammonium chloride
customevaporated
customThe crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 100/0 to 97/3

Sources & evidence

ORD record: ord-fe558e529f0d4d1290929aafa7d5b9b8
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452897B2

Reaction notes

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