3-Bromoaniline → N-(3-bromophenyl)pyrido[4,3-d]pyrimidin-4-amine

HRID 50778Notes

Reaction equation

HRID 50778 reaction equation
CS[C:3]1[C:4]2[CH:12]=[N:11][CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>>[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH:17][C:3]1[C:4]2[CH:12]=[N:11][CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 115623-BromoanilineHCID 106548874-Methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328249N-(3-bromophenyl)pyrido[4,3-d]pyrimidin-4-amineYield 10%

Procedure

A mixture of 4-methylthiopyrido[4,3-d]pyrimidine (171 mg, 0.96 mmol), (see previous experimental) and 3-bromoaniline (1 mL) is heated to i00C for 2 h. A solid precipitates on cooling and is collected by vacuum filtration and then recrystallized from EtOH to yield 4-(3-bromoanilino)pyrido[4,3-d]pyrimidine (30 mg, 10%). 1H NMR (DMSO) δ 10.33 (1H, s), 9.86 (1H, s), 8.84 (1H, d, J=5.8 Hz), 8.79 (1H, s), 8.22 (1H, s), 7.89 (1H, d, J=7.2 Hz), 7.69 (1H, d, J=5.8 Hz), 7.40 (2H, dt, Jd=8.0 Hz, Jt=1.5 Hz).

Workup

  1. temperatureis heated to i00C for 2 h
  2. customA solid precipitates
  3. temperatureon cooling
  4. filtrationis collected by vacuum filtration
  5. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-42f87c03d75f4050a203ced7a5349245
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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