Potassium Carbonate → 2-Methylpentane

HRID 347750Notes

Reaction equation

HRID 347750 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([Cl:11])[N:6]=1.[F:17][C:18]([F:24])([F:23])[CH2:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:2][CH2:3][CH2:12][CH:13]([CH3:16])[CH3:14].[Cl:11][C:7]1[N:6]=[C:5]([N:4]([CH2:21][CH2:20][CH2:19][C:18]([F:24])([F:23])[F:17])[C:3]2[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:2]=2[F:1])[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 17981132HCID 17981132, compound

Product 2

HCID 78922-MethylpentaneHCID 21083743HCID 21083743, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Fluoro-5-methylanilino)-2chloropyrimidine (Reference Example A-10, 750 mg, 3.16 mmol), 4,4,4-trifluoro-1-bromobutane (725 mg, 3.80 mmol) and potassium carbonate (525 mg, 3.80 mmol) were dissolved in DMF (3 ml). The reaction mixture was stirred at room temperature for 12 hours and then 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 (976 mg). NMR (300 MHz, 373K): 1.79 (m, 2H), 2.28 (m, 2H), 2.33 (s, 3H), 3.91 (t, 2H), 6.19 (d, 1H), 7.28 (m, 3H), 8.03 (d, 1H); m/z (EI+) 347 (M+).

Workup

  1. customevaporated onto silica (5 ml)
  2. custompurified by column chromatography
  3. washeluting with EtOAc (0–40%)

Sources & evidence

ORD record
ord-9c28941c1e734f7b8af3054097a7da8a
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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