N-(3-bromophenyl)-7-fluoropyrido[4,3-d]pyrimidin-4-amine → N-(3-bromophenyl)-7-methoxypyrido[4,3-d]pyrimidin-4-amine

HRID 1059596Notes

Reaction equation

HRID 1059596 reaction equation
F[C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH3:20][O-:21].[Na+].CO>>[CH3:20][O:21][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 5328251N-(3-bromophenyl)-7-fluoropyrido[4,3-d]pyrimidin-4-amineHCID 23694274Sodium methanolate methanol

Product 1

HCID 5328254N-(3-bromophenyl)-7-methoxypyrido[4,3-d]pyrimidin-4-amineYield 89%

Procedure

A solution of 7-fluoro-4-(3-bromoanilino)pyrido[4,3-d]pyrimidine (100 mg, 0.31 mmol) in 1 M sodium methoxide-methanol (30 mL) is stirred under reflux for 42 h. The resulting mixture is concentrated under reduced pressure, diluted with water and neutralized with dilute HCl to give 7-methoxy-4-(3-bromoanilino)pyrido[4,3-d]pyrimidine (92 mg, 89%) as a white solid. 1H NMR (DMSO) δ 10.22 (1H, brs), 9.57 (1H, s), 8.63 (1H, s), 8.19 (1H, s), 7.86 (1H, brd, J=7.9 Hz), 7.39 (1H, t, J=7.9 Hz), 7.35 (1H, dd, J=7.9, 1.5 Hz), 6.96 (1H, s), 4.00 (3H, s).

Workup

  1. temperatureunder reflux for 42 h
  2. concentrationThe resulting mixture is concentrated under reduced pressure
  3. additiondiluted with water and neutralized with dilute HCl

Sources & evidence

ORD record
ord-db2e568fb2104d28bcd41025f64459b6
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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