Sodium borohydride → 2-(4,6-Dichloropyrimidin-5-yl)ethan-1-ol

Temperature

0 °C

(4,6-dichloropyrimidin-5-yl)acetaldehyde (2.96 g, 15.5 mmol) was dissolved in methanol (60 mL) and cooled at 0° C. Sodium tetrahydroborate (0.879 g, 23.2 mmol) was added and the mixture was stirred for 1 hour. TLC indicated complete conversion. The reaction was quenched with water (20 mL), methanol was removed in vacuo and the residue was extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The residue was purified using chromatography on silica gel using gradient 0 to 100% ethyl acetate in methylene chloride to afford the title compound (1.90 g, 63%). LC/MS: Rt=0.93 min, ES+ 194 (AA standard).

1. customThe reaction was quenched with water (20 mL), methanol
2. customwas removed in vacuo
3. extractionthe residue was extracted with ethyl acetate (3×30 mL)
4. dry with materialThe combined organic extracts were dried with magnesium sulfate
5. filtrationfiltered
6. customevaporated
7. customThe residue was purified

ORD record

ord-bfae48d08d964ea68c1dd90f3231234e

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008307B2