Phosphorus oxychloride → 4-Chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine
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]=1Participants
3
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
- extractionextracted twice with ethyl acetate
- washThe organic phases are washed three times with water and brine
- dry with material