3-Chloroaniline → 4-(3-Chloro-anilino)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 369856Notes

Reaction equation

HRID 369856 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>C(O)CCC.CN1C(=O)N(C)CCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH:21][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 79323-ChloroanilineHCID 224844424-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 99051784-(3-Chloro-anilino)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

A suspension of 1.251 g (5.45 mmol) of 4-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine and 1.15 ml (10.9 mmol) of 3-chloro-aniline in 20 ml of n-butanol and 0.5 ml of DMPU is heated at boiling for 2 hours. The reaction mixture is cooled and filtered. Stirring of the residue in hot THF/methanol yields the title compound; m.p. 285-286° C.; FAB-MS: (M+H)+ =321.

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-cc7c3d072056483bbd490e35c7107d83
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

Loading…