3-Methoxybenzylamine → 4-N-[(3-methoxyphenyl)methyl]pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 2287717Notes

Reaction equation

HRID 2287717 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][O:15][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]([O:15][CH3:14])[CH:17]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 211563-MethoxybenzylamineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280884-N-[(3-methoxyphenyl)methyl]pyrido[4,3-d]pyrimidine-4,7-diamineYield 77%

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 3-methoxybenzylamine (1.37 g, 10.0 mmol) in isopropanol (3 mL) is stirred under N2 at reflux for 3 h. Evaporation of the solvent and chromatography on silica gel (5-10% EtOH/EtOAc) gives 7-amino-4-(3-methoxybenzylamino)pyrido[4,3-d]pyrimidine (153 mg, 77%) as a white solid. 1H NMR (DMSO) δ 9.11 (1H, s), 8.83 (1H, t, J=5.7 Hz), 8.26 (1H, s), 7.24 (1H, dt, Jd =0.8 Hz, Jt =8.1 Hz), 6.92 (2H, m), 6.81 (1H, dt, Jd =8.2 Hz, Jt =1.2 Hz), 6.46 (2H, brs), 6.37 (1H, s), 4.71 (2H, d, J=5.8 Hz), 3.73 (3H, s).

Workup

  1. temperatureat reflux for 3 h
  2. customEvaporation of the solvent and chromatography on silica gel (5-10% EtOH/EtOAc)

Sources & evidence

ORD record
ord-6d9b45bf192544338dbc9d8d774a306c
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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