Imidazole → ethyl (RS)-2-chloro-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate

HRID 1088302Notes

Reaction equation

S(Cl)([Cl:3])=O.O[C:6]([C:16]1[CH:17]=[N:18][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[N:20][CH:21]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].N1C=CN=C1.O>C(#N)C>[Cl:3][C:6]([C:16]1[CH:17]=[N:18][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[N:20][CH:21]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Thionyl chloride (0.57 g) was added dropwise to a solution of ethyl (RS)-2-hydroxy-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate (0.2 g) and imidazole (0.32 g) in dry acetonitile (7 cm3), whilst the reaction temperature was maintained at 0° C. The mixture was allowed to warm to the ambient temperature and stirred for a period of sixteen hours, after which time it was poured into water, and extracted into dichloromethane. The combined organic extracts were washed with water, dried over anhydrous magnesium sulphate, passed through a short plug of silica, and concentrated by evaporation of the solvent under reduced pressure to give ethyl (RS)-2-chloro-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate as a yellow oil (0.15 g).

Workup

temperatureto warm to the ambient temperature
extractionextracted into dichloromethane
washThe combined organic extracts were washed with water
dry with materialdried over anhydrous magnesium sulphate
concentrationconcentrated by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-68c698323c26477c8864b43368e59027
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04962109

Reaction notes

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