Cyclohexanol → Cyclohexyl 2,4-dichloropyrimidine-6-carboxylate

A cold (0° C.) solution of cyclohexanol (3.82 ml; 36.2 mmol) was treated with sodium hydride (869 mg; 36.2 mmol) in dry THF (100 ml) and stirred for 30 min at 0° C. It was slowly added to a cooled (0° C.) solution of methyl 2,4-dichloropyrimidine-6-carboxylate (Apollo, 10.00 g; 48.3 mmol) in dry THF (200 ml) and the resulting mixture was stirred for 24 h. The reaction mixture was concentrated under vacuum. The residue was taken up in EtOAc and the organic layer was washed with water, then brine, dried over MgSO4, filtered off and concentrated under vacuum to afford a crude which was purified by flash chromatography eluting with cHex-EtOAc 8:2 to afford the title compound as a white solid.

1. additionIt was slowly added to
2. stirringthe resulting mixture was stirred for 24 h
3. concentrationThe reaction mixture was concentrated under vacuum
4. washthe organic layer was washed with water
5. dry with materialbrine, dried over MgSO4
6. filtrationfiltered off
7. concentrationconcentrated under vacuum
8. customto afford a crude which
9. customwas purified by flash chromatography
10. washeluting with cHex-EtOAc 8:2

ORD record

ord-1657971618a042ada3873319581a3399

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150519B2