m-Chloroperbenzoic acid → [6-(Methylsulfinyl)-4-pyrimidinyl]acetonitrile

To a suspension of [6-(methylthio)-4-pyrimidinyl]acetonitrile (Intermediate 15, 292 mg, 1.767 mmol) in DCM (15 mL) was added 3-chloroperoxybenzoic acid (457 mg, 2.65 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and kept stirring for 3 hours. The reaction mixture was quenched with saturated sodium thiosulfate solution (10 mL) and vigorously stirred for 30 minutes, then treated with DCM (75 mL). The reaction mixture was partitioned between DCM and water. The organic layer was washed with saturated ammonium carbonate solution, water and brine sequentially, then dried over sodium sulfate, concentrated under pressure to give the title compound as a brown solid (150 mg);

1. customThe reaction mixture was quenched with saturated sodium thiosulfate solution (10 mL)
2. stirringvigorously stirred for 30 minutes
3. additiontreated with DCM (75 mL)
4. customThe reaction mixture was partitioned between DCM and water
5. washThe organic layer was washed with saturated ammonium carbonate solution, water and brine sequentially
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under pressure

ORD record

ord-2357ec3dc19048d887ecb8d1519a5c82

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2