Cyclohexanol → Cyclohexyl 2-chloro-6-(cyclohexyloxy)pyrimidine-4-carboxylate

Temperature

0 °C

A cold (0° C.) solution of cyclohexanol (2.35 ml; 22.3 mmol) was treated with sodium hydride (534 mg; 22.3 mmol) in dry THF (25 ml) and stirred for 30 min at 0° C. It was slowly added to a cooled (0° C.) solution of cyclohexyl 2,6-dichloropyrimidine-4-carboxylate (Intermediate 31, 3.50 g; 12.72 mmol) in dry THF (70 ml) and the resulting mixture was stirred at 50° C. After 4 h the reaction was treated again with a solution cyclohexanol (0.34 ml; 3.18 mmol) and sodium hydride (76.3 mg; 3.18 mmol) in dry THF (3 mL) obtained as described above and it was stirred for an additional hour. The reaction mixture was concentrated under vacuum and 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 the title compound (4.80 g, 99%) without further purification.

1. additionIt was slowly added to
2. stirringthe resulting mixture was stirred at 50° C
3. customobtained
4. stirringwas stirred for an additional hour
5. concentrationThe reaction mixture was concentrated under vacuum
6. washthe organic layer was washed with water
7. dry with materialbrine, dried over MgSO4
8. filtrationfiltered off
9. concentrationconcentrated under vacuum

ORD record

ord-87b0a2e778bd45b39c6e260ca6f864eb

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150519B2