3-Bromoaniline → 7-Amino-4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidine

HRID 2256133Notes

Reaction equation

HRID 2256133 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: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]([Br:14])[CH:16]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 115623-BromoanilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 3820597-Amino-4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidine

Conditions

Temperature
190 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (167 mg, 0.87 mmol) (described in a previous experimental) and 3-bromoaniline (0.75 mL, 7.8 mmol) is stirred under N2 at 190° C. for 2.5 h, and the precipitate which appears on cooling is recrystallized from PriOH. 1H NMR (DMSO) δ 9.91 (1H, brs), 9.34 (1H, s), 8.45 (1H, s), 8.19 (1H, s), 7.84 (1H, d, J=8.0 Hz), 7.34 (1H, t, J=8.0 Hz), 7.29 (1H, d, J=8.2 Hz), 6.68 (2H, brs), 6.45 (1H, s).

Workup

  1. temperatureon cooling
  2. customis recrystallized from PriOH

Sources & evidence

ORD record
ord-c649cf1b4b084cc09503fc054c6cc835
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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