4-(Trifluoromethyl)benzylamine → Pyrido[4,3-d]pyrimidine-4,7-diamine,n4-[[4-(trifluoromethyl)phenyl]methyl]-

HRID 50816Notes

Reaction equation

HRID 50816 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.[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:21][CH2:20][C:19]3[CH:18]=[CH:17][C:16]([C:15]([F:14])([F:24])[F:25])=[CH:23][CH:22]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328086Pyrido[4,3-d]pyrimidine-4,7-diamine,n4-[[4-(trifluoromethyl)phenyl]methyl]-Yield 56.2%

Conditions

Temperature
140 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (225 mg, 1.17 mmol) and 4-(trifluoromethyl)benzylamine (0.63 mL, 4.42 mmol) is stirred under N2 at 140° C. for 1 h. The resulting product is chromatographed on alumina (5-10% EtOH/CHCl3) then silica gel (2-10% EtOH/EtOAc) to give 7-amino-4-[(4-trifluoromethylphenyl) methylamino]pyrido[4,3-d]pyrimidine (0.21 g, 56%) as a light brown solid. 1H NMR (DMSO) δ 9.12 (1H, s), 8.94 (1H, t, J=5.8 Hz), 8.24 (1H, s), 7.69 (2H, d, J=8.1 Hz), 7.56 (2H, d, J=8.1 Hz), 6.48 (2H, brs), 6.38 (1H, s), 4.82 (2H, d, J=5.8 Hz).

Workup

  1. customThe resulting product is chromatographed on alumina (5-10% EtOH/CHCl3)

Sources & evidence

ORD record
ord-d16ffa4b1aa9453e9095a4fe09f20eed
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

Loading…