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-cd5551f7f35444d0abf193a41b49fc09
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952331

Reaction notes

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