Hydrochloric Acid → 1-(6-Methyl-2-(phenylamino)pyrimidin-4-yl)propan-2-one

HRID 2166246Notes

Reaction equation

HRID 2166246 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+]([O-])(O)=O.[C:11]1([NH:17][C:18]([NH2:20])=[NH:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:21][C:22]1[O:29]C(=O)[CH:26]([C:30]([CH3:32])=O)[C:24](=O)[CH:23]=1.Cl>CN(C)C=O>[NH:17]([C:18]1[N:20]=[C:30]([CH3:32])[CH:26]=[C:24]([CH2:23][C:22]([CH3:21])=[O:29])[N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 122903Dehydroacetic acidHCID 178418691HCID 178418691, compound

Product 1

HCID 146741421-(6-Methyl-2-(phenylamino)pyrimidin-4-yl)propan-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 500 ml reaction flask equipped with a stirrer, a thermometer and a condenser, 200 ml of dimethylformamide, 13.8 g (0.1 mol) of potassium carbonate, 39.6 g (0.2 mol) of phenylguanidine nitrate and 33.6 g (0.2 mol) of dehydroacetic acid were charged, and the reaction was conducted at 140° C. for 3 hours. After completion of the reaction, the reaction solution was cooled and put into ice water. Then, the reaction solution was extracted with toluene and washed with water. Then, 21 g (0.2 mol) of concentrated hydrochloric acid was dropwise added thereto. Precipitated crystals were collected by filtration, washed with toluene, then neutralized with an aqueous sodium carbonate solution and again extracted with toluene. This toluene layer was washed with water and concentrated to obtain 24.1 g of 2-anilino-4-methyl-6-acetonyl-pyrimidine having a melting point of from 77° to 80° C. The yield was 50%.

Workup

  1. customInto a 500 ml reaction flask
  2. customequipped with a stirrer
  3. customAfter completion of the reaction
  4. temperaturethe reaction solution was cooled
  5. extractionThen, the reaction solution was extracted with toluene
  6. washwashed with water
  7. customPrecipitated crystals
  8. filtrationwere collected by filtration
  9. washwashed with toluene
  10. extractionagain extracted with toluene
  11. washThis toluene layer was washed with water
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-becfb5fbedc64640a21c19932210f385
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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