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

HRID 369838Notes

Reaction equation

HRID 369838 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27]>C(O)CCC>[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH:27][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 857171974-Chloro-6-(biphen-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 1317221334-(3-Chloro-anilino)-6-(biphen-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 220 mg (0.72 mmol) of 4-chloro-6-(biphen-4-yl)-7H-pyrrolo[2,3-d]-pyrimidine and 151 μl (1.44 mmol) of 3-chloro-aniline in 5 ml of butanol is heated at boiling overnight. Cooling, filtering and washing with a large amount of ethanol and, finally, hexane yield the title compound; 1H-NMR (200 MHz, DMSO-d6): 12.46 (sb, 1H), 9.6 (s, 1H), 8.40 (s, 1H), 8.28 (m, 1H), 7.98 (d, J=8, 2H), 7.8 (m, 5H), 7.52 and 7.38 (2t, J=8, each 2H), 7.30 (s, 1H), 7.08 (db, J=8, 1H); MS: (M)+ =397.

Workup

  1. temperatureis heated
  2. temperatureCooling
  3. filtrationfiltering
  4. washwashing with a large amount of ethanol

Sources & evidence

ORD record
ord-e768f99f5da245e2a82c20502c6dfd51
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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