2-Bromoaniline → 4-N-(2-bromophenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 50792

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

Participants

Reactant 2

HCID 119922-Bromoaniline

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

Product 1

HCID 53280554-N-(2-bromophenyl)pyrido[4,3-d]pyrimidine-4,7-diamineYield 33.2%

Conditions

Temperature: 180 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (198 mg, 1.03 mmol) (described in a previous experimental) and 2-bromoaniline (1.00 mL, 9.18 mmol) is stirred under N2 at 180° C. for 2.5 h, and the resulting product is chromatographed on alumina (1% EtOH/CHCl3) to give 7-amino-4-(2-bromoanilino)pyrido[4,3-d]pyrimidine (108 mg, 33%) as a pale yellow solid, 1H NMR (DMSO) δ 9.91 (1H, brs), 9.27 (1H, s), 8.20 (1H, s), 7.73 (1H, d, J=7.9 Hz), 7.50 (1H, m), 7.44 (1H, t, J=6.9 Hz), 7.25 (1H, m), 6.59 (2H, brs), 6.42 (1H, s).

Workup

customthe resulting product is chromatographed on alumina (1% EtOH/CHCl3)

Sources & evidence

ORD record: ord-7aabd9d42fcc4be08d55aaaaf2ebeace
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713484B2

Linked notes

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