O-Toluidine → 2-(2-Methylphenylamino)-4-(N-methylphenylamino)thieno[2,3-d]pyrimidine hydrochloride

HRID 1198114Notes

Reaction equation

HRID 1198114 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1.[NH2:19][C:20]1[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1>CO>[ClH:1].[CH3:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][C:2]1[N:3]=[C:4]([N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 103560572-Chloro-4-(N-methylphenylamino)thieno[2,3-d]pyrimidine

Product 1

HCID 678504012-(2-Methylphenylamino)-4-(N-methylphenylamino)thieno[2,3-d]pyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-4-(N-methylphenylamino)thieno[2,3-d]pyrimidine (1.5 g, 0.0054 mol) and o-toluidine (1.3 g, 0.012 mol) were heated at 160° in an oil bath for 2 hours. The addition of methanol gave a solid which was collected by filtration and dried. Recrystallization from ethanolic HCl gave the title compound as a partial hydrochloride salt, (1.13 g), m.p. 210°-212°.

Workup

  1. customgave a solid which
  2. filtrationwas collected by filtration
  3. customdried
  4. customRecrystallization from ethanolic HCl

Sources & evidence

ORD record
ord-ab6f9e43779641068b4d43b162cb37db
Source dataset
uspto-grants-1994_01
Patent number
US05280026

Reaction notes

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