Aniline → HCID 178433114, compound

HRID 1371220Notes

Reaction equation

HRID 1371220 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCO>[ClH:1].[CH3:8][C:6]1[NH:5][C:4]2[C:3]([N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=2)=[C:2]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:7]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433114HCID 178433114, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 5-mL, wheaton vial were added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1 (e)) (100 mg, 0.41 mmol) and aniline (Aldrich Chemical Company) (0.37 mL, 4.1 mmol), followed by EtOH (1.5 mL). The reaction was heated at reflux for 4 h. The reaction mixture was allowed to cool to room temperature and the precipitate was collected by filtration, washed with hexanes, dried in a vacuum oven overnight to give 114 mg of a brown solid. The material was recrystallized from EtOH to give 57 mg (41%) of the title compound as an off-white solid. 1H NMR (DMSO-d6; 400 MHz): d 2.67 (s, 3), 7.04 (s, 1), 7.21-7.23 (m, 1), 7.44-7.59 (m, 5), 8.03 (d, 2, J=8.0), 8.15 (d, 2, J=8.0), 11.61 (br s, 1), 13.84 (br s, 1). MS m/z: 301 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 4 h
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with hexanes
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-c153ee227a1d44b9978235e382f7a56f
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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