Water → N-(3-bromophenyl)-7-methoxypyrido[2,3-d]pyrimidin-4-amine

HRID 50840Notes

Reaction equation

HRID 50840 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[CH:15]=[CH:14][C:13](F)=[N:12][C:8]=2[N:9]=[CH:10][N:11]=1.[CH3:20][O-:21].[Na+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[CH:15]=[CH:14][C:13]([O:21][CH3:20])=[N:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5328268N-(3-bromophenyl)-7-fluoropyrido[2,3-d]pyrimidin-4-amineHCID 10942334Sodium Methoxide

Product 1

HCID 5328271N-(3-bromophenyl)-7-methoxypyrido[2,3-d]pyrimidin-4-amineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(3-bromoanilino)-7-fluoropyrido[2,3-d]pyrimidine (0.26 g, 0.81 mmol) and sodium methoxide (prepared from 75 mg of sodium, 3.26 mmol) in dry MeOH (15 mL) is heated at 90° C. in a pressure vessel for 18 h. The mixture is poured into water and extracted with EtOAc to give 4-(3-bromoanilino)-7-methoxypyrido[2,3-d]pyrimidine (0.23 g, 86%). 1H NMR (DMSO) δ 9.88 (1H, brs), 8.82 (1H, d, J=8.9 Hz), 8.71 (1H, s), 8.18 (1H, dd, J=8.0, 1,9 Hz), 7.36 (1H, dd, J=8.1, 8.0 Hz), 7.29 (1H, ddd, J=8.1, 1.9, 1,9 Hz) 7.15 (1H, d, J=8.9 Hz), 4.01 (3H, s).

Workup

  1. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-0fa2f573888e45dabfa9b9ecd965b750
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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