2-(Aminomethyl)aniline → 4-N-[(2-aminophenyl)methyl]pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 50807Notes

Reaction equation

HRID 50807 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.[NH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18]>C(O)(C)C>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:18][CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[NH2:14])=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 1780962-(Aminomethyl)anilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280904-N-[(2-aminophenyl)methyl]pyrido[4,3-d]pyrimidine-4,7-diamineYield 47.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (136 mg, 0.71 mmol) (described in a previous experimental) and 2-aminobenzylamine (1.70 g, 13.8 mmol) in isopropanol (5 mL) is stirred at reflux for 1 h, and the resulting product is chromatographed on silica gel (7-20% EtOH/EtOAc) and alumina (6-10i EtOH/CHCl3) to give 7-amino-4-(2-aminobenzylamino)pyrido[4,3-d]pyrimidine (89 mg, 47%) as a white solid. 1H NMR (DMSO) δ 9.08 (1H, s), 8.68 (1H, t, J=5.8 Hz), 8.26 (1H, s), 7.05 (1H, d, J=7.4 Hz), 6.96 (1H, t, J=7.6 Hz), 6.63 (1H, d, J=7.9 Hz), 6.51 (1H, t, J=7.4 Hz), 6.46 (2H, brs), 6.35 (1H, s), 5.20 (2 H, brs), 4.56 (2H, d, J=5.8 Hz).

Workup

  1. temperatureat reflux for 1 h
  2. customthe resulting product is chromatographed on silica gel (7-20% EtOH/EtOAc) and alumina (6-10i EtOH/CHCl3)

Sources & evidence

ORD record
ord-00b2002f949b45f49006c6d5f022bf42
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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