Ammonium Hydroxide → (4-(4-Fluorophenyl)pyrimidin-5-yl)methanamine

HRID 1749401Notes

Reaction equation

HRID 1749401 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]#[N:15])=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[NH4+].[H][H]>CO.[Ni]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14][NH2:15])=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 118162104HCID 118162104, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 83700631(4-(4-Fluorophenyl)pyrimidin-5-yl)methanamineYield 32%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-fluorophenyl)pyrimidine-5-carbonitrile (1.0 equiv.) and Raney-nickel (20 mol %) in MeOH (0.1 M) was degassed under vacuum and followed by the addition of 30% ammonium hydroxide (10 equiv.). The resulting mixture was hydrogenated with hydrogen gas at room temperature overnight. The mixture was filtered through a pad of celite and the cake was rinsed with MeOH. The filtrate was concentrated and further dried to give a brown oil, which was purified by silica gel column chromatography (0-10% MeOH in DCM, 25 g column) to give the title compound (32% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 9.19 (s, 1H), 8.88 (s, 1H), 7.71-7.78 (m, 2H), 7.17-7.24 (m, 2H), 3.99 (s, 2H), 1.41 (br. s., 2H). MS (ESI) m/z 204.1 [M+1]+.

Workup

  1. customwas degassed under vacuum
  2. filtrationThe mixture was filtered through a pad of celite
  3. washthe cake was rinsed with MeOH
  4. concentrationThe filtrate was concentrated
  5. customfurther dried
  6. customto give a brown oil, which
  7. customwas purified by silica gel column chromatography (0-10% MeOH in DCM, 25 g column)

Sources & evidence

ORD record
ord-6ebdaf5250954c0bb3e67495264b8b4f
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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