Potassium Carbonate → 4-[3'-(2,3-Epoxypropoxy)anilino]6-(3'-methylanilino) pyrimidine

HRID 1418004Notes

Reaction equation

HRID 1418004 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[NH:5][C:6]1[CH:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[N:9]=[CH:8][N:7]=1.Br[CH2:24][CH:25]1[O:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[O:27]1[CH2:26][CH:25]1[CH2:24][O:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[NH:5][C:6]1[CH:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 54524025HCID 54524025, compound

Product 1

HCID 867538554-[3'-(2,3-Epoxypropoxy)anilino]6-(3'-methylanilino) pyrimidineYield 38%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-[3'-hydroxyanilino]6-(3'-methylanilino)pyrimidine (1 g), 1-bromo-2,3-epoxypropane (0.44 ml) and potassium carbonate (0.95 g) in DMSO (12 ml) was stirred at ambient temperature overnight. The reaction mixture was diluted with water and extracted with methylene chloride. The organic layer was washed with water, dried (MgSO4) and evaporated to give 4-[3'-(2,3-epoxypropoxy)anilino]6-(3'-methylanilino)pyrimidine in 38% yield, m.p. 143°-145° C.;

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-91c7be3c91f84f298cbc35371a40cfa6
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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