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

HRID 50815

Reaction equation

HRID 50815 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:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20]>>[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]([C:15]([F:14])([F:24])[F:25])[CH:17]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 759623-(Trifluoromethyl)benzylamineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328085Pyrido[4,3-d]pyrimidine-4,7-diamine,n4-[[3-(trifluoromethyl)phenyl]methyl]-Yield 64.2%

Conditions

Temperature
140 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (225 mg, 1.17 mmole) and 3-(trifluoromethyl)benzylamine (0.63 mL, 4.40 mmole) is stirred under N2 at 140° C. for 1 h. The resulting product is chromatographed on silica gel (3-5t EtOH/EtOAc) to give 7-amino-4-[(3-trifluoromethylphenyl)methylamino]pyrido[4,3-d]pyrimidin (0.24 g, 63%) as a light brown solid. 1H NMR (DMSO) δ 9.10 (1H, s), 8.92 (1H, t, J=5.7 Hz), 8.26 (1H, s), 7.71 (1H, s), 7.66 (1H, d, J=7.4 Hz), 7.62 (1H, d, J=7.8 Hz), 7.57 (1H, t, J=7.6 Hz), 6.49 (2H, brs), 6.38 (1H, s), 4.82 (2H, d, J=5.8 Hz).

Workup

  1. customThe resulting product is chromatographed on silica gel (3-5t EtOH/EtOAc)

Sources & evidence

ORD record
ord-7460375d32394aeb8f646e4306e924f4
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Linked notes

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