Aniline → N-phenyl-9H-pyrimido[4,5-b]indol-4-amine

HRID 1358288Notes

Reaction equation

HRID 1358288 reaction equation
Cl.Cl[C:3]1[C:4]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[NH:16]([C:3]1[C:4]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:5]=2[N:6]=[CH:7][N:8]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 181843914-Chloroindolo[2,3-d]pyrimidine hydrochloride

Product 1

HCID 5328391N-phenyl-9H-pyrimido[4,5-b]indol-4-amineYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloroindolo[2,3-d]pyrimidine hydrochloride (R. G. Glushkov et. al., Khim.-Farm. Zh., 1967, 1(9), 25-32) (240 mg, 1 mmol) and aniline (0.27 mL, 3 mmol) in ethanol (1 mL) are heated under reflux for 6 h. The solvent is evaporated under reduced pressure, and the residue triturated with EtOAc to afford a tan powder which is filtered, and washed with cold ethanol. Recrystallization from acetone/pet. ether gives 4-anilinoindolo[2,3-d]pyrimidine (49 mg, 19%). 1H NMR (DMSO) δ1H, s), 8.84 (1H, s), 8.43 (1H, s), 8.37 (1H, d, J=8.0 Hz), 7.74 (2H, d, J=7.7 Hz), 7.52-7.08 (6H, m).

Workup

  1. temperatureunder reflux for 6 h
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue triturated with EtOAc
  4. customto afford a tan powder which
  5. filtrationis filtered
  6. washwashed with cold ethanol
  7. customRecrystallization from acetone/pet. ether

Sources & evidence

ORD record
ord-28fa885dd44f491cabbe2cf1e5a4ef4c
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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