3-Methoxyaniline → 4-N-(3-methoxyphenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 2287689Notes

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.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:22][C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH3:14])[CH:17]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 108243-Methoxyaniline

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

Product 1

HCID 53280614-N-(3-methoxyphenyl)pyrido[4,3-d]pyrimidine-4,7-diamineYield 43.1%

Conditions

Temperature: 190 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (226 mg, 1.18 mmol) (described in the previous experimental) and m-anisidine (1.00 mL, 8.90 mmol) is stirred under N2 at 190° C. for 1.5 h. The resulting product is chromatographed over silica gel (5-7% EtOH/EtOAc) to give 7-amino-4-(3-methoxyanilino)pyrido[4,3-d]pyrimidine (136 mg, 43%) as a light brown solid. 1H NMR (DMSO) δ 9.78 (1H, brs), 9.34 (1H, s), 8.40 (1H, s), 7.50 (1H, brs), 7.44 (1H, d, J=8.0 Hz), 7.28 (1H, t, J=8.2 Hz), 6.71 (1H, dd, J=8.2, 2.3 Hz), 6.61 (2H, brs), 6.45 (1H, s), 3.77 (3H, s).

Workup

customThe resulting product is chromatographed over silica gel (5-7% EtOH/EtOAc)

Sources & evidence

ORD record: ord-d917f8843d7e45238a9f4a3b49715c04
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06084095

Reaction notes

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