4-Methylpyrimidine-2-carbonitrile → 4-Methyl-2-pyrimidinemethanamine

HRID 1911839Notes

Reaction equation

HRID 1911839 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1)#[N:2].[H][H]>CO.[Pd]>[CH3:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:1][NH2:2])[N:8]=1

Participants

5

Reactant 2

HCID 126843244-Methylpyrimidine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 187277634-Methyl-2-pyrimidinemethanamineYield 91.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a nitrogen flushed solution of the title compound from Step A (1 g, 8.39 mmol) in methanol (40 ml) was added 10% palladium on carbon (100 mg) and the resulting mixture stirred under a balloon of hydrogen for 3 h. The mixture was filtered through celite and evaporated to give 950 mg (91%) of the title compound (i-6) as an orange oil. 1HNMR (CDCl3): 2.54 (s, 3H), 4.16 (s, 2H), 7.03 (d, J5.0 Hz, 1H), 8.56 (d, J5.0 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-c28d958338364ca6be669962cd3ea4e2
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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