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

HRID 1749501Notes

Reaction equation

HRID 1749501 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 filtrated was concentrated in vacuo and purified by silica gel column chromatography (5% MeOH in DCM) to afford the desired product (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 filtrated was concentrated in vacuo
  3. custompurified by silica gel column chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-7711ffc75d4348c9bfb5709a96c2b002
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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