HCID 20562710, compound → HCID 20562714, compound

HRID 1155071Notes

Reaction equation

HRID 1155071 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH2:19][CH3:20])=[CH:6][N:5]=[CH:4][N:3]=1>P(Cl)(Cl)(Cl)=O>[CH2:19]([O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[C:9]1[NH:8][C:7]2[C:2](=[N:3][CH:4]=[N:5][CH:6]=2)[N:1]=1)[CH3:20]

Participants

3

Reactant 1

HCID 20562710HCID 20562710, compound

Product 1

HCID 20562714HCID 20562714, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

An amount of 2.3 g of 4-amino-5-(2-ethoxy-4-methoxybenzoylamino)-pyrimidine was refluxed in 20 ml of phosphorus oxychloride for 2.5 hours. The reaction mixture was poured on ice, and the solid product formed was filtered off. The filtrate was made alkaline by means of sodium bicarbonate and extracted with ethyl acetate. After evaporation of the ethyl acetate phases, the residue was combined with the solid product obtained above and purified by chromatography on silicagel (eluate: methylene chloride/ethanol in volume ratio of from 100:0 to 97:3).

Workup

  1. additionThe reaction mixture was poured on ice
  2. customthe solid product formed
  3. filtrationwas filtered off
  4. extractionextracted with ethyl acetate
  5. customAfter evaporation of the ethyl acetate phases
  6. customobtained above and
  7. custompurified by chromatography on silicagel (eluate: methylene chloride/ethanol in volume ratio of from 100:0 to 97:3)

Sources & evidence

ORD record
ord-545778e5142646bf9505cdf7e2f799a8
Source dataset
uspto-grants-1981_11
Patent number
US04299834

Reaction notes

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