Diisobutylaluminum hydride → 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde

HRID 1482483Notes

Reaction equation

HRID 1482483 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[N:8]=[CH:7][C:6]([C:9](OCC)=[O:10])=[CH:5][N:4]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[F:15][C:2]([F:1])([F:14])[C:3]1[N:4]=[CH:5][C:6]([CH:9]=[O:10])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 21936133Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 177509412-(Trifluoromethyl)pyrimidine-5-carbaldehydeYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-trifluoromethyl-pyrimidine-5-carboxylate (1 g, 5 mmol) in DCM (23 mL) at −78° C. was added DIBAL-H (6 ml, 6 mmol, 1.0 M solution in toluene) slowly and stirred at the same temperature for 3 h. The mixture was quenched with slow addition of 2M hydrochloric acid and warmed to room temperature. The mixture was extracted with EtOAc (3×20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give the title compound (572 mg, yield: 71.5%). 1H NMR (CDCl3 400 MHz): ppm 10.27 (s, 1H), 9.35 (s, 2H).

Workup

  1. customThe mixture was quenched with slow addition of 2M hydrochloric acid
  2. extractionThe mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e0261a7863db4766be9e48a79f01ebc2
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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