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

HRID 1059613Notes

Reaction equation

HRID 1059613 reaction equation
CS[C:3]1[C:4]2[CH:12]=[CH:11][N: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]=[CH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 115623-BromoanilineHCID 232404654-Methylthiopyrido[3,4-d]pyrimidine

Product 1

HCID 5328257N-(3-bromophenyl)pyrido[3,4-d]pyrimidin-4-amineYield 52.7%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-methylthiopyrido[3,4-d]pyrimidine (75 mg, 0.42 mmol) (see previous experimental), and 3-bromoaniline (1 mL) is heated to 100° C. under N2 for 2 h. The reaction mixture is then chromatographed on silica using MPLC and eluting with a gradient system (CHCl3 to 5% MeOH in CHCl3). The fractions are concentrated under reduced pressure, and the resulting solid is recrystallized from Et2O to yield 4-(3-bromoanilino)pyrido[3,4-d]pyrimidine (66 mg, 52.7%) as a light brown solid. 1H NMR (DMSO) δ 10.15 (1H, s), 9.21 (1H, s), 8.80 (1H, s), 8.76 (1H, d, J=5.8 Hz), 8.44 (1H, d, J=5.6 Hz), 8.25 (1H, s), 7.93 (1H, d, J=7.7 Hz), 7.45-7.37 (2H, m).

Workup

  1. customThe reaction mixture is then chromatographed on silica using MPLC
  2. washeluting with a gradient system (CHCl3 to 5% MeOH in CHCl3)
  3. concentrationThe fractions are concentrated under reduced pressure
  4. customthe resulting solid is recrystallized from Et2O

Sources & evidence

ORD record
ord-6c51576c6d3741a0a4229db66d49a308
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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