Diisobutylaluminumhydride → 2-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde

Temperature

-78 °C

Diisobutyl aluminum hydride (1.21 mL, 1M solution in hexane, 1.22 mmol), was added dropwise to a solution of ethyl 2-chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carboxylate (242 mg, 0.81 mmol) in dry dichloromethane (10 mL) under nitrogen at −78° C. The mixture was stirred at −78° C. for 1 h. Diisobutyl aluminum hydride solution (1 mL) was added and the mixture was stirred for 15 minutes. The mixture was quenched with methanol and allowed to reach ambient temperature. Water (10 mL) and dichloromethane were added, the pH of the water phase was adjusted to 6 by addition of acetic acid. The mixture was filtered through a pad of silica gel and sodium bicarbonate. The water phase was extracted with 5% solution of methanol in dichloromethane (3×10 mL). The combined organic phase was dried over sodium sulfate and concentrated in vacuum to yield the title product, 216 mg (100%).

1. stirringthe mixture was stirred for 15 minutes
2. customThe mixture was quenched with methanol
3. customto reach ambient temperature
4. additionWater (10 mL) and dichloromethane were added
5. additionthe pH of the water phase was adjusted to 6 by addition of acetic acid
6. filtrationThe mixture was filtered through a pad of silica gel and sodium bicarbonate
7. extractionThe water phase was extracted with 5% solution of methanol in dichloromethane (3×10 mL)
8. dry with materialThe combined organic phase was dried over sodium sulfate
9. concentrationconcentrated in vacuum

ORD record

ord-d81bfd85ad7d446a8ef515ada0c5ba1a

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09439904B2