Chlorodifluoromethane → 2-Methylthio-4-difluoromethoxy-6-methylpyrimidine

HRID 1719783Notes

Reaction equation

[CH3:1][S:2][C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[N:4]=1.[OH-].[Na+].[F:13][CH:14]([F:16])Cl>O1CCOCC1>[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][CH:14]([F:16])[F:13])[CH:6]=[C:5]([CH3:10])[N:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

218.7 g (1.4 mols) of 2-methylthio-4-hydroxy-6-methylpyrimidine are suspended in 1.12 litres of dioxane, and 1500 g (11.2 mols) of 30% aqueous sodium hydroxide solution are added. The suspension is heated to 80° C., and into this hot suspension are passed, in the course of 3 hours, 242 g (2.8 mols) of difluorochloromethane. The pale yellow suspension obtained is cooled to 20° C. and filtered. The residue is washed with dioxane and dried to thus yield 210 g of 2-methylthio-4-difluoromethoxy-6-methylpyrimidine. The filtrate is extracted with methylene chloride, and the organic phase is washed with water and concentrated by evaporation to obtain, as crystalline residue, a further 79 g of the desired product. The overall yield obtained in this manner is 289 g of 2-methylthio-4-difluoromethoxy-6-methylpyrimidine (100% of theory), m.p. 40-42° C.

Workup

customThe pale yellow suspension obtained
temperatureis cooled to 20° C.
filtrationfiltered
washThe residue is washed with dioxane
dry with materialdried to thus yield 210 g of 2-methylthio-4-difluoromethoxy-6-methylpyrimidine
extractionThe filtrate is extracted with methylene chloride
washthe organic phase is washed with water
concentrationconcentrated by evaporation
customto obtain, as crystalline residue

Sources & evidence

ORD record: ord-bc8fcc8e4ddc43ec916f8421c6b6e4e5
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04542216

Reaction notes

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