3-Nitroaniline → 7-Amino-4-(3-nitroanilino)pyrido[4,3-d]pyrimidine

HRID 2256128

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

Participants

Reactant 2

HCID 74233-Nitroaniline

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

Product 1

HCID 53280537-Amino-4-(3-nitroanilino)pyrido[4,3-d]pyrimidineYield 43.5%

Conditions

Temperature: 200 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (127 mg, 0.66 mmol) (described in a previous experimental) and 3-nitroaniline (1.70 g, 12.3 mmol) is stirred under N2 at 200° C. for 1.5 h. The resulting product is chromatographed over alumina (5-20% EtOH/CHCl3) to give 7-amino-4-(3-nitroanilino)pyrido[4,3-d]pyrimidine (81 mg, 39%) as a brown solid. 1H NMR (DMSO) δ 10.17 (1H, brs), 9.37 (1H, s), 8.87 (1H, brs), 8.48 (1H, s), 8.33 (1H, brd, J=7.5 Hz), 7.95 (1H, ddd, J=8.2, 2.1, 1.0 Hz), 7.67 (1H, t, J=8.2 Hz), 6.70 (2H, brs), 6.47 (1H, s).

Workup

customThe resulting product is chromatographed over alumina (5-20% EtOH/CHCl3)

Sources & evidence

ORD record: ord-552d276e0f4344ab95ffbde8c96db9a1
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654307

Linked notes

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