Water → 2-(2-Chloro-5-fluoro-phenyl)-5-methyl-7-propoxy-oxazolo[5,4-d]pyrimidine

HRID 1027474Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH3:10].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C:19]1[O:20][C:21]2[N:22]=[C:23]([CH3:29])[NH:24][C:25](=[O:28])[C:26]=2[N:27]=1.O>CN(C)C=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C:19]1[O:20][C:21]2[N:22]=[C:23]([CH3:29])[N:24]([CH2:8][CH2:9][CH3:10])[C:25](=[O:28])[C:26]=2[N:27]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C:19]1[O:20][C:21]2[N:22]=[C:23]([CH3:29])[N:24]=[C:25]([O:28][CH2:8][CH2:9][CH3:10])[C:26]=2[N:27]=1

Participants

Conditions

Temperature: 60 °C

Procedure

26.2 g of potassium carbonate and 6.4 g of 1-bromo-propane were added to a solution of 15 g of 2-(2-chloro-5-fluoro-phenyl)-5-methyl-6H-oxazolo[5,4-d]pyrimidin-7-one in 150 ml of dimethylformamide. The suspension was stirred at 60° C. for 72 h. After cooling, the mixture was poured onto 300 ml of water. The precipitate was filtered off by suction. The obtained mixture of regioisomers was separated by silica gel chromatography (method SC1). Besides 3.3 g of 2-(2-chloro-5-fluoro-phenyl)-5-methyl-6-propyl-6H-oxazolo[5,4-d]pyrimidin-7-one, 3.2 g of the title compound were obtained.

Workup

temperatureAfter cooling
filtrationThe precipitate was filtered off by suction
additionThe obtained mixture of regioisomers
customwas separated by silica gel chromatography (method SC1)

Sources & evidence

ORD record: ord-3406bfff8bd24ed7b5b4d251f868162f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735387B2

Reaction notes

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