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

HRID 705950
Notes
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Reaction equation

HRID 705950 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:9][C:8]([F:11])([F:10])[C:5]1[N:4]=[CH:3][C:2](/[CH:14]=[CH:13]/[C:12]([O:16][CH3:17])=[O:15])=[CH:7][N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 336979635-Bromo-2-(trifluoromethyl)pyrimidine

Product 1

HCID 21936364methyl (2E)-3-[2-(trifluoromethyl)-5-pyrimidinyl]-2-propenoateYield 98%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-bromo-2-(trifluoromethyl)pyrimidine (900 mg, 3.97 mmol), methyl 2-propenoate (0.533 mL, 5.95 mmol), Pd(OAc)2 (44.5 mg, 0.198 mmol), tri-o-tolylphosphine (241 mg, 0.793 mmol) and TEA (1.105 mL, 7.93 mmol) in DMF (6 mL) under argon was heated at 130° C. for 1 h. After cooling to room temperature, water (40 mL) was added to the reaction mixture and then extracted by EA (3×50 mL). The organic phase was washed with brine, dried over MgSO4 and evaporated in vacuo to afford the title compound (900 mg, 3.88 mmol, 98% yield) as a yellow solid. LCMS: rt=2.67 min, [M+H+]=233

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted by EA (3×50 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b6b915b6fcc941649beb9ad9379077c6
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174968B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes