Methanesulfonyl chloride → (2-Chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate

HRID 59078Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[CH2:16])[N:8]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][S:2]([O:14][CH2:13][C:11]1[CH:10]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[CH2:16])[N:8]=[C:7]([Cl:6])[N:12]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (0.369 mL, 4.73 mmol) was added to an ice-cold solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methanol (846 mg, 3.94 mmol) in DCM (8 mL) containing N,N-diisopropylethylamine (1.0 mL, 5.91 mmol). The mixture was stirred at 0° C. for 10 min. DCM (30 mL) was added and the mixture was washed with water (5 mL). The organic phase was dried over sodium sulfate, filtered and the solvent was evaporated to give the title compound (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (1249 mg, quant.).

Workup

washthe mixture was washed with water (5 mL)
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-40593e2a0654432e8c3879c3a0bc7659
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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