methyl (2E)-3-[2-(trifluoromethyl)-5-pyrimidinyl]-2-propenoate → Methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoate

HRID 705951

Reaction equation

HRID 705951 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])=[CH:5][N:4]=1>CO.[Pd]>[F:16][C:2]([F:1])([F:15])[C:3]1[N:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][N:8]=1

Participants

4

Reactant 1

HCID 21936364methyl (2E)-3-[2-(trifluoromethyl)-5-pyrimidinyl]-2-propenoate

Product 1

HCID 21936211Methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoateYield 65.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl (2E)-3-[2-(trifluoromethyl)-5-pyrimidinyl]-2-propenoate (870 mg, 3.75 mmol) and Pd/C (39.9 mg, 0.375 mmol) in methanol (4 mL) was stirred at room temperature for 1 h under hydrogen. After cooling, the mixture was filtered through silica gel. The filtrate was concentrated to afford the title compound (577 mg, 2.47 mmol, 65.8% yield). LCMS: rt=2.47 min, [M+H+]=235

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through silica gel
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-50408753688142e789ed2b7c03a55cc2
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Linked notes

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