Phosphorus oxychloride → 1H-Purine, 8-(2-methoxy-4-(methylthio)phenyl)-

HRID 1155065Notes

Reaction equation

HRID 1155065 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:9]([NH2:10])=[CH:8][N:7]=[CH:6][N:5]=1.[CH3:11][O:12][C:13]1[CH:21]=[C:20]([S:22][CH3:23])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=O.P(Cl)(Cl)(Cl)=O>C(O)C>[CH3:11][O:12][C:13]1[CH:21]=[C:20]([S:22][CH3:23])[CH:19]=[CH:18][C:14]=1[C:15]1[NH:10][C:9]2[C:4](=[N:5][CH:6]=[N:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 27595912-Methoxy-4-(methylthio)benzoyl chlorideHCID 20562693Pyrimidine-4,5-diamine dihydrochloride

Product 1

HCID 30599131H-Purine, 8-(2-methoxy-4-(methylthio)phenyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.1 g of 4,5-diamino-pyrimidine dihydrochloride, 7.1 g of 2-methoxy-4-methylmercapto-benzoylchloride, and 50 ml of phosphorus oxychloride was refluxed for three hours. The reaction mixture was evaporated until one-half of the original volume remained, and then the remaining mixture was poured into water. The precipitate that formed was dissolved in boiling ethanol, precipitated by addition of ether, and purified by chromatography on silicagel (eluate: methylene chloride/ethanol in a volume ratio of 19:1).

Workup

  1. temperaturewas refluxed for three hours
  2. customThe reaction mixture was evaporated until one-half of the original volume
  3. additionthe remaining mixture was poured into water
  4. customThe precipitate that formed
  5. dissolutionwas dissolved
  6. customprecipitated by addition of ether
  7. custompurified by chromatography on silicagel (eluate: methylene chloride/ethanol in a volume ratio of 19:1)

Sources & evidence

ORD record
ord-6f2ce2ad1fe448d69a3bf21d73a91289
Source dataset
uspto-grants-1981_11
Patent number
US04299834

Reaction notes

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