Potassium Carbonate → N-(2-dimethylaminoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxamide

HRID 255718Notes

Reaction equation

HRID 255718 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([OH:25])=O.S(Cl)(Cl)=O.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH2:34].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.ClCCl>[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH:34][C:23]([C:3]1[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[N:5][C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:7][C:2]=1[CH3:1])=[O:25]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 151474876-Methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid

Product 1

HCID 10319094N-(2-dimethylaminoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid (9 g), dichloromethane (72 ml) and N,N-dimethylformamide (20 ml), thionyl chloride (2.1 ml) was added at 7° C. under ice cooling. After stirring for 1.5 hours at the same condition, 2-dimethylaminoethylamine (5.9 g) was added and stirred for 2 hours. The reaction mixture was adjusted to pH=8.5 by saturated potassium carbonate and extracted with chloroform. The organic layer was washed with water and brine and dried over magnesium sulfate. The solvent was distilled off to give a residue, which was chromatographed on alumina eluting with a mixture of n-hexane and ethyl acetate (5:1). The fractions containing the desired product were combined and concentrated in vacuo. The crystalline residue was recrystallized from diethyl ether to afford N-(2-dimethylaminoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxamide.

Workup

  1. additionwas added at 7° C. under ice cooling
  2. additionwas added
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customto give a residue, which
  8. customwas chromatographed on alumina eluting with a mixture of n-hexane and ethyl acetate (5:1)
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated in vacuo
  11. customThe crystalline residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-34435b4c07e94ad596d90f2ca64fd052
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

Loading…