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

HRID 1092667Notes

Reaction equation

HRID 1092667 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-94416f07961841c08a679b17498aabaf
Source dataset
uspto-grants-2012_03
Patent number
US08129526B2

Reaction notes

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