4-(1-Fluoro-1-methylethyl)-5-pyrimidinecarbonitrile → HCID 82417295, compound

HRID 1749415Notes

Reaction equation

HRID 1749415 reaction equation
F[C:2]([C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:4])[CH3:3]>C1COCC1.[Ni]>[CH:2]([C:5]1[C:10]([CH2:11][NH2:12])=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 726991554-(1-Fluoro-1-methylethyl)-5-pyrimidinecarbonitrile

Product 1

HCID 82417295HCID 82417295, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2-fluoropropan-2-yl)pyrimidine-5-carbonitrile (1.0 equiv.) and Raney-nickel in THF (0.5 M) was degassed under vacuum. The resulting mixture was hydrogenated under a fully-inflated balloon 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 (0-20% MeOH in ethyl acetate, 50 g column) to give (30% yield) of pale yellow oil as a 3:2 mixture of the above two products. MS (ESI) m/z 152.0 [M+1]+. MS (ESI) m/z 170.0 [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 (0-20% MeOH in ethyl acetate, 50 g column)

Sources & evidence

ORD record
ord-0cd64cc10eec491793f7c67711590c11
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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