(Bis(2-methoxyethyl)amino)sulfur trifluoride → 2-Chloro-4-(1-fluoroethyl)pyrimidine

HRID 595157Notes

Reaction equation

COCCN(S(F)(F)[F:11])CCOC.[Cl:14][C:15]1[N:20]=[C:19]([CH:21](O)[CH3:22])[CH:18]=[CH:17][N:16]=1>ClCCl>[Cl:14][C:15]1[N:20]=[C:19]([CH:21]([F:11])[CH3:22])[CH:18]=[CH:17][N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Bis(2-methoxyethyl)aminosulfur trifluoride (7.70 g, 17.4 mmol) was added drop wise to a solution of 1-(2-chloropyrimidin-4-yl)ethanol (2.30 g, 14.5 mmol) in dichloromethane (20 mL) at 0° C. and the mixture was stirred at 0° C. for 15 minutes. The mixture was diluted with dichloromethane and washed with aqueous sodium bicarbonate. The organic layers were separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane) to afford 2-chloro-4-(1-fluoroethyl)pyrimidine. 1H NMR (500 MHz, DMSO-d6) δ 8.66 (d, J=5.0 Hz, 1H), 7.45 (d, J=5.0 Hz, 1H), 5.65-5.51 (m, 1H), 1.71-1.65 (m, 3H).

Workup

washwashed with aqueous sodium bicarbonate
customThe organic layers were separated
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane)

Sources & evidence

ORD record: ord-635abef2763c4090bd8afc9471d6f12b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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