(Diethylamino)sulfur trifluoride → 4-Chloro-6-(1-fluoroethyl)pyrimidine

HRID 2401191Notes

Reaction equation

C(N(S(F)(F)[F:7])CC)C.[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([CH:17](O)[CH3:18])[CH:12]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]([F:7])[CH3:18])[N:14]=[CH:15][N:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(Diethylamino)sulphur trifluoride (0.337 mL, 2.55 mmol) was added to DCM (13 mL), cooled to −78° C. and treated dropwise with a solution of 1-(6-chloro-4-pyrimidinyl)ethanol (Intermediate 20, 328 mg, 2.068 mmol) in DCM (4 mL) under argon. The resulting mixture was allowed to warm to room temperature and stirred for 4 hours. The reaction was quenched by adding water (5 mL) and extracted with DCM (×2). The DCM layers were separated, combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-25% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil (125 mg);

Workup

temperatureto warm to room temperature
customThe reaction was quenched
additionby adding water (5 mL)
extractionextracted with DCM (×2)
customThe DCM layers were separated
customdried under magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by column chromatography (Biotage SP4)
washeluting with a gradient of 0-25% ethyl acetate and iso-hexane
additionProduct containing fractions
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-f943ac1ae97049739ab8e741e84fc117
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796283B2

Reaction notes

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