HCID 18507439, compound → HCID 18507409, compound

HRID 1355809Notes

Reaction equation

HRID 1355809 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]#[N:15])=[C:4]([CH:16]=[CH2:17])[N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[N:3]=[C:4]([CH2:16][CH3:17])[C:5]([C:14]#[N:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

Participants

5

Reactant 2

HCID 18507439HCID 18507439, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18507409HCID 18507409, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 100 mg (0.45 mmol) 2-amino-4-phenyl-6-vinyl-pyrimidine-5-carbonitrile in 10 ml ethanol was stirred with a spatula end of 10% palladium on charcoal under 1 atm of hydrogen for 16 h at room temperature. After filtration to remove the catalyst, the reaction mixture was concentrated in vacuo and the residue triturated in ether to afford 35 mg (35%) 2-amino-4-ethyl-6-phenyl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 224 (M+, 44), 223 ([M—H]+, 100).

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe residue triturated in ether

Sources & evidence

ORD record
ord-ea183c9c1a1b4019bea1f1eeb39dd8c7
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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