Phosphorus oxychloride → 4-Chloro-6-methyl-2-(methylthio)pyrimidine

Reaction equation

O[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178503447HCID 178503447, compound

Product 1

HCID 2411634-Chloro-6-methyl-2-(methylthio)pyrimidineYield 80%

Procedure

4-Hydroxy-6-methyl-2-(methylthio)pyrimidine (9.20 g, 59 mmol) and phosphorous oxychloride (60 mL) were combined and refluxed for 3 hours. The reaction mixture was cooled to room temperature and poured onto crushed ice. The resultant aqueous mixture was extracted with ethyl acetate; and the organic layer washed with saturated aqueous sodium bicarbonate followed by a water wash, dried over magnesium sulfate, and dried in vacuo to give 4-chloro-6-methyl-2-(methylthio)pyrimidine (8.27 g, 80%), m.p. 37°-38° C.

Workup

temperaturerefluxed for 3 hours
additionpoured
customonto crushed ice
extractionThe resultant aqueous mixture was extracted with ethyl acetate
washand the organic layer washed with saturated aqueous sodium bicarbonate
washwash
dry with materialdried over magnesium sulfate
customdried in vacuo

Sources & evidence

ORD record: ord-98a5dd7fdda34899b5a9b85033b0fa91
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863924

Reaction notes

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