O-Xylene → 4,5-Diphenyl-2-(methylamino)pyrimidine

HRID 1271261Notes

Reaction equation

HRID 1271261 reaction equation
CN(C)C=[C:4](C1C=CC=CC=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.Cl.[CH3:21][NH:22][C:23]([NH2:25])=[NH:24].[C:26](=O)([O-])[O-].[K+].[K+].[C:32]1(C)[C:33](C)=[CH:34][CH:35]=[CH:36][CH:37]=1>O>[C:32]1([C:21]2[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:4][N:24]=[C:23]([NH:25][CH3:26])[N:22]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 11430Potassium CarbonateHCID 865033-(Dimethylamino)-1,2-diphenyl-2-propen-1-oneHCID 178485118HCID 178485118, compound

Product 1

HCID 229319754,5-Diphenyl-2-(methylamino)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.00 g of 3-(dimethylamino)-1,2-diphenyl-2-propen-1-one, 6.90 g of 1-methylguanidine hydrochloride and 8.70 g of potassium carbonate were added to 20 ml of xylene and then heated at reflux for 13 hours using a reflux condenser equipped with a Dean-Stark water separator. The reaction solution was extracted with ethyl acetate after adding water, dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The crude crystal was washed with diisopropyl ether and dried to obtain 6.51 g of the desired compound as a pale yellow crystal having a melting point of 136 to 138° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 13 hours
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. additionafter adding water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. washThe crude crystal was washed with diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-ea8297476e2241909b49efbdc6d6d24b
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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