3-(aminomethyl)-N,N-dimethylaniline → Pyrido[4,3-d]pyrimidine-4,7-diamine,n4-[[3-(dimethylamino)phenyl]methyl]-

HRID 2256147Notes

Reaction equation

HRID 2256147 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](SC)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH3:14][N:15]([CH3:24])[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20]>C(O)(C)C>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[C:16]([N:15]([CH3:24])[CH3:14])[CH:17]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 27609383-(aminomethyl)-N,N-dimethylanilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328094Pyrido[4,3-d]pyrimidine-4,7-diamine,n4-[[3-(dimethylamino)phenyl]methyl]-Yield 40%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (236 mg, 1.23 mmol) (described in a previous experimental) and 3-dimethylamino-benzylamine (1.36 g, 9.07 mmol) in isopropanol (5 mL) is stirred under N2 at reflux for 1 h, and the resulting product is chromatographed on silica gel (10-15% EtOH/EtOAc), then on alumina (1% EtOH/CHCl3) to give 7-amino-4-(3-dimethylaminobenzylamino)pyrido[4,3-d]pyrimidine (145 mg, 40%) as a white solid. 1H NMR (DMSO) δ 9.11 (1H, s), 8.79 (1H, t, J=5.9 Hz), 8.26 (1H, s), 7.11 (1H, dd, J=8.0, 7.7 Hz), 6.73 (1H, brs), 6.63 (1H, d, J=7.6 Hz), 6.60 (1H, dd, J=8.1, 2.2 Hz), 6.44 (2H, brs), 6.35 (1H, s), 4.67 (2H, d, J=5.8 Hz), 2.86 (6H, s).

Workup

  1. temperatureat reflux for 1 h
  2. customthe resulting product is chromatographed on silica gel (10-15% EtOH/EtOAc)

Sources & evidence

ORD record
ord-478981fc33f145d984724b75036ee301
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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