Chloroacetonitrile → 2-Methylpentane

HRID 347743Notes

Reaction equation

HRID 347743 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[Br:16])[CH:5]=[CH:4][N:3]=1.Cl[CH2:18][C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:9][CH2:10][CH2:11][CH:12]([CH3:15])[CH3:13].[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:18][C:19]#[N:20])[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[Br:16])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 7856Chloroacetonitrile2×HCID 11430Potassium Carbonate2×HCID 17981144HCID 17981144, compound

Product 2

HCID 78922-MethylpentaneHCID 21083745HCID 21083745, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-4-(2-bromo-4-methylanilino)pyrimidine (500 mg, 1.68 mmol), chloroacetonitrile (0.13 ml, 2.02 mmol) and potassium carbonate (279 mg, 2.02 mmol) were dissolved in DMF (3 ml). The reaction mixture was stirred at room temperature for 12 hours. Chloroacetonitrile (0.13 ml, 2.02 mmol) and potassium carbonate (279 mg, 2.02 mmol) were again added, and the reaction mixture was stirred at room temperature for a further 48 hours. The reaction mixture was evaporated onto silica (5 ml) and purified by column chromatography eluting with EtOAc (0–40%):isohexane to give the title product as a solid on evaporation (537 mg). NMR (300 MHz): 2.38 (s, 3H), 4.82 (d, 1H), 4.99 (d, 1H), 6.09 (brs, 1H), 7.41 (m, 2H), 7.71 (s, 1H), 8.16 (brd, 1H); M.S. (ES+) 337.2 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for a further 48 hours
  2. customThe reaction mixture was evaporated onto silica (5 ml)
  3. custompurified by column chromatography
  4. washeluting with EtOAc (0–40%)

Sources & evidence

ORD record
ord-c0eda7544a2349f488a9b4baaeb63fdb
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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