4-(2,2-Difluoropropoxyl)pyrimidine-5-carbonitrile → C-[4-(2,2-Difluoro-propoxy)-pyrimidin-5-yl]-methylamine

HRID 1749520Notes

Reaction equation

HRID 1749520 reaction equation
[F:1][C:2]([F:14])([CH3:13])[CH2:3][O:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][N:6]=1>C1COCC1.[Ni]>[F:14][C:2]([F:1])([CH3:13])[CH2:3][O:4][C:5]1[C:10]([CH2:11][NH2:12])=[CH:9][N:8]=[CH:7][N:6]=1

Participants

4

Reactant 1

HCID 1181620714-(2,2-Difluoropropoxyl)pyrimidine-5-carbonitrile

Product 1

HCID 118162151C-[4-(2,2-Difluoro-propoxy)-pyrimidin-5-yl]-methylamineYield 37.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2,2-difluoropropoxyl)pyrimidine-5-carbonitrile (1.7 g, 8.54 mmol) in THF (30 mL) was added Raney nickel (500 mg, crude). The resulting mixture was stirred at room temperature overnight under hydrogen atmosphere. The reaction was filtered and the filtrate was concentrated in vacuo to give the crude product, which was purified by silica gel column chromatography (5% MeOH in DCM) to afford the title compound (650 mg, 3.20 mmol, 37% yield) as a yellow solid. MS (ESI) m/z 204.1 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give the crude product, which
  4. customwas purified by silica gel column chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-c4664033052d407bb757a9c44ed154ba
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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