N-Methylaniline → 2,4-Bis(N-methylphenylamino)thieno(2,3-d)pyrimidine

HRID 1198117Notes

Reaction equation

HRID 1198117 reaction equation
Cl[C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)(Cl)Cl>[CH3:12][N:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[N:3]=[C:4]([N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 122173242,4-Dichlorothieno[2,3-d]pyrimidine

Product 1

HCID 103156292,4-Bis(N-methylphenylamino)thieno(2,3-d)pyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2,4-Dichlorothieno[2,3-d]pyrimidine (2 g, 0.00975 mol) and N-methylaniline (5 ml) were heated in an oil bath at 150° for 2 hours. The reaction mixture was dissolved in chloroform (200 ml) and extracted with 2N hydrochloric acid (3×100 ml). The chloroform solution was then washed with sodium carbonate solution, dried over magnesium sulphate, filtered and evaporated to give an oil. The oil was purified by chromatography using dichloromethane as eluant. The solid obtained was recrystallized from ether/petroleum ether (b.p. 40°-60°) to give the title compound, (1.2 g) m.p. 85°-87°.

Workup

  1. extractionextracted with 2N hydrochloric acid (3×100 ml)
  2. washThe chloroform solution was then washed with sodium carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil
  7. customThe oil was purified by chromatography
  8. customThe solid obtained
  9. customwas recrystallized from ether/petroleum ether (b.p. 40°-60°)

Sources & evidence

ORD record
ord-feea85f7879d4eb4abbffa364b47048a
Source dataset
uspto-grants-1994_01
Patent number
US05280026

Reaction notes

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