Dimethylformamide → 4-(2-Butynyloxy)-6-(2-methyl-pyrrolidin-1-yl)pyrimidine

HRID 14530

Reaction equation

HRID 14530 reaction equation
CN(C)C=O.Cl[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]#[C:16][CH3:17])[N:10]=[CH:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][CH:25]1[CH2:29][CH2:28][CH2:27][NH:26]1>C(OCC)(=O)C>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([N:26]2[CH2:27][CH2:28][CH2:29][CH:25]2[CH3:24])[N:8]=[CH:9][N:10]=1)[C:15]#[C:16][CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 587017944-(2-Butynyloxy)-6-(2-methyl-pyrrolidin-1-yl)pyrimidineYield 89.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate and 85 mg of 2-methylpyrrolidine was added therein, and the mixture was stirred for 7 hours at 60° C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 207 mg of 4-(2-butynyloxy)-6-(2-methyl-pyrrolidin-1-yl) pyrimidine (hereinafter, referred to as Compound (21)).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to near room temperature
  3. washthe mixture was washed with a saturated sodium chloride aqueous solution three times
  4. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f6e7397cfab14baf90d86a8479bbe747
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Linked notes

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