Thionyl Chloride → HCID 22349860, compound

Reaction equation

[C:1]([C:5]1[N:10]=[C:9](O)[CH:8]=[C:7]([CH:12]([F:14])[F:13])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:17])=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:5]1[N:10]=[C:9]([Cl:17])[CH:8]=[C:7]([CH:12]([F:14])[F:13])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Procedure

2.8 g of 2-tert-butyl-4-hydroxy-6-difluoromethyl-pyrimidine (13.9 mmol) and 3 ml of thionylchloride were stirred 14 h at room temperature and an additional 3 h at 76° C. 20 ml of dichloromethane were added with cooling, followed by addition of 15 ml of a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate and the solvent was evaporated to yield the crude title compound which was purified by column chromatography on silica gel (dichloromethane/hexane 1:1) to yield 0.8 g of product.