Dimethylformamide → 4-(2-Butynyloxy)-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine

HRID 14536Notes

Reaction equation

HRID 14536 reaction equation
CN(C)C=O.[CH2:6]([O:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1)[C:7]#[C:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[CH3:24][C:25]1([CH3:30])[CH2:29][CH2:28][NH:27][CH2:26]1>C(OCC)(=O)C>[CH2:6]([O:10][C:11]1[CH:16]=[C:15]([N:27]2[CH2:28][CH2:29][C:25]([CH3:30])([CH3:24])[CH2:26]2)[N:14]=[CH:13][N:12]=1)[C:7]#[C:8][CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 121376024-(2-Butynyloxy)-6-chloropyrimidineHCID 149492113,3-Dimethylpyrrolidine

Product 1

HCID 593411434-(2-Butynyloxy)-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidineYield 22.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into 4 ml of N,N-dimethylformamide was resolved 0.37 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.56 g of potassium carbonate and 0.2 g of 3,3-dimethylpyrrolidine was added therein, and the mixture was stirred for 6 hours at 80%. 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 0.11 g of 4-(2-butynyloxy)-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine (hereinafter, referred to as Compound (27)).

Workup

  1. additionwas added
  2. washthe mixture was washed with a saturated sodium chloride aqueous solution three times
  3. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-37bb723d4f1a41838bbae86778df26a3
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Reaction notes

Loading…