Water → ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-fluoropyrimidin-5-yl]-3-methylbutyrate

HRID 34597Notes

Reaction equation

[F-:1].[K+].[CH3:3][C:4]([C:7]1[N:12]=[C:11](Cl)[C:10]([CH:14]([CH:20]([CH3:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][N:8]=1)([CH3:6])[CH3:5].C1OCCOCCOCCOCCOCCOC1.O>S1(CCCC1)(=O)=O>[CH3:3][C:4]([C:7]1[N:12]=[C:11]([F:1])[C:10]([CH:14]([CH:20]([CH3:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][N:8]=1)([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred suspension of dry potassium fluoride (1.41 g) and ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-chloropyrimidin-5-yl]-3-methylbutyrate (1.88 g) in dry sulpholane (14 cm3) in the presence of 18-crown-6 (0.38 g) was heated to 150° C. for a period of 24 hours, under an atmosphere of dry nitrogen. After cooling to the ambient temperature (ca. 22° C.), the reaction mixture was poured into water, and extracted into ethyl acetate. The organic layer was washed with water and brine, dried and the solvent evaporated under reduced pressure. The residual brown liquid was purified by column chromatography on silica gel, using dichloromethame as eluent, to give ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-fluoropyrimidin-5-yl]-3-methylbutyrate (0.8 g) as an orange liquid.

Workup

temperatureAfter cooling to the ambient temperature (ca. 22° C.)
extractionextracted into ethyl acetate
washThe organic layer was washed with water and brine
customdried
customthe solvent evaporated under reduced pressure
customThe residual brown liquid was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-bc70d94a32264df591934f2084d3e64c
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04762835

Reaction notes

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