3-Iodoaniline → 4-N-(3-iodophenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 50795

Reaction equation

HRID 50795 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.[I:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[C:15]([I:14])[CH:16]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 122713-IodoanilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280714-N-(3-iodophenyl)pyrido[4,3-d]pyrimidine-4,7-diamineYield 61.8%

Conditions

Temperature
160 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (72 mg, 0.37 mmol) and 3-iodoaniline (1.25 g, 5.71 mmol) is stirred at 160° C. for 30 min. The resulting product is chromatographed over silica gel (5-7% MeOH/CH2Cl2) to give 7-amino-4-(3-iodoanilino)pyrido[4,3-d]pyrimidine (83 mg, 61%) as a light brown rosettes. 1H NMR (DMSO) δ 9.84 (1H, brs), 9.34 (1H, s), 8.44 (1H, s), 8.30 (1H, brs), 7.90 (1H, dd, J=7.9, 0.8 Hz), 7.47 (1H, d, J=7.7 Hz), 7.18 (1H, t, J=8.0 Hz), 6.66 (2H, brs), 6.46 (1H, s).

Workup

  1. customThe resulting product is chromatographed over silica gel (5-7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-17ff54742ec440b3aa2bf9ac26c61100
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Linked notes

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