Ammonium Hydroxide → 5-(Aminomethyl)-4-phenylpyrimidin-2-amine

HRID 1749420Notes

Reaction equation

HRID 1749420 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])=[CH:4][N:3]=1.[OH-].[NH4+]>C1COCC1.[Ni]>[NH2:15][CH2:14][C:5]1[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 7236882-Amino-4-phenylpyrimidine-5-carbonitrile

Product 1

HCID 1181621585-(Aminomethyl)-4-phenylpyrimidin-2-amineYield 56%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-phenylpyrimidine-5-carbonitrile (1.0 equiv.) in THF (0.15 M) was added ammonium hydroxide and Raney nickel. The mixture was stirred at room temperature under hydrogen atmosphere overnight and then the reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to give the crude title compound (56% yield) as a yellow solid. The product was used without further purification. 1H-NMR (300 MHz, DMSO-d6) δ (ppm) 8.34 (s, 1H), 7.69-7.65 (m, 2H), 7.46-7.44 (m, 3H), 6.50 (br, 2H), 3.54 (s, 2H), 1.70 (br, 2H); MS (ESI) m/z=201.2 [M+1]+.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-15c109e6d9d144b9b8b9893e7a331a6c
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

Loading…