Phosphorus oxychloride → 4-Chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369853Notes

Reaction equation

HRID 369853 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:18][C:12]3[N:13]=[CH:14][N:15]=[C:16](O)[C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:16]1[C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[NH:18][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488432HCID 178488432, compound

Product 1

HCID 232824574-Chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine

Procedure

With the exclusion of moisture, 121 mg (0.50 mmol) of 6-(4-methoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol and 1 ml of phosphorus oxychloride are heated at boiling for 1.5 hours. The reaction mixture is poured into ice-water and extracted twice with ethyl acetate. The organic phases are washed three times with water and brine, dried with MgSO4 and concentrated by evaporation. Stirring of the residue in diethyl ether yields the title compound; m.p. 248-249OC; FAB-MS: (M+H)+ =260.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phases are washed three times with water and brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-594c30bd64bb468c953d25c5dbfbd29c
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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