HCID 66832503, compound → HCID 66832666, compound

HRID 1914520Notes

Reaction equation

HRID 1914520 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=2)=[CH:5][CH:4]=1>C(O)C.[Pd]>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([CH2:15][NH2:16])[CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 66832503HCID 66832503, compound

Product 1

HCID 66832666HCID 66832666, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of solution of 6-(4-trifluoromethyl-phenyl)-pyrimidine-4-carbonitrile (1.34 g, 5.37 mmol) in ethanol (40 mL) was added 10% Pd/C (700 mg) and the reaction mixture was placed under a H2 atmosphere (55 psi) for 3 hours. The reaction mixture was filtered through a pad of celite and concentrated to provide the desired product (1.3 g, 97%). 1H NMR (400 MHz, CDCl3) δ 9.23 (d, J=1.2, 1H), 8.23 (d, J=8.1, 2H), 7.83 (s, 1H), 7.77 (d, J=8.2, 2H), 4.08 (s, 2H), 1.59 (s, 2H).

Workup

  1. customfor 3 hours
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-84feb96a497b44539b240e97d461d19a
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

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