3-(Trifluoromethyl)aniline → 4-N-[3-(trifluoromethyl)phenyl]pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 1281945Notes

Reaction equation

HRID 1281945 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:16]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:19][CH:20]=1>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280584-N-[3-(trifluoromethyl)phenyl]pyrido[4,3-d]pyrimidine-4,7-diamineYield 42.2%

Conditions

Temperature
195 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (234 mg, 1.22 mmol) (described in a previous experimental) and 3-aminobenzotrifluoride (2.00 mL, 16.0 mmol) is stirred under N2 at 190-200° C. for 2 h, and the resulting product is then chromatographed over silica gel (5-10% EtOH/EtOAc), and then over alumina (5-7% EtOH/CHCl3) to give 7-amino-4-(3-trifluoromethylanilino)pyrido[4,3-d]pyrimidine (157 mg, 42%) as a cream solid. 1H NMR (DMSO) δ 10.04 (1H, s), 9.37 (1H, s), 8.46 (1H, s), 8.31 (1H, s), 8.19 (1H, d, J=8.2 Hz), 7.62 (1H, t, J=8.0 Hz), 7.45 (1H, d, J=7.7 Hz), 6.69 (2H, brs), 6.47 (1H, s).

Workup

  1. customthe resulting product is then chromatographed over silica gel (5-10% EtOH/EtOAc)

Sources & evidence

ORD record
ord-49846d38d01648fa8a6aad9da9c39b58
Source dataset
uspto-grants-2002_09
Patent number
US06455534B2

Reaction notes

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