Diisopropylethylamine → Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate

HRID 1909116Notes

Reaction equation

HRID 1909116 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.C(N(C(C)C)CC)(C)C>C(O)C.[Pd]>[F:16][C:13]([F:14])([F:15])[C:4]1[N:3]=[CH:2][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 2737166Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 21936133Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylateYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate (30.2 g, 119.0 mmol) in ethanol (594 mL) under nitrogen were added palladium (10% on carbon, 50% water wet; 2.58 g, 1.21 mmol) and diisopropylethylamine (50.0 mL, 286.0 mmol). The mixture stirred under hydrogen (1 atm). After 6 h, the mixture was filtered with Celite. The filtrate was concentrated and ethyl acetate was added. The mixture was washed with sat. NaHCO3 (2×), brine, dried over Na2SO4, filtered and concentrated to give the title compound (25.6 g). MS 221.1 (M+1).

Workup

  1. filtrationthe mixture was filtered with Celite
  2. concentrationThe filtrate was concentrated
  3. additionethyl acetate was added
  4. washThe mixture was washed with sat. NaHCO3 (2×), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d5d30a561409401e81dd5117e0b61a4e
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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