2,4-Dimethoxybenzylamine → 3-benzyl-6-(2,4-dimethoxy-benzylamino)-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

HRID 1749096Notes

Reaction equation

HRID 1749096 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12]2[N:14]=[C:15](F)[CH:16]=[CH:17][C:11]=2[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31]>>[CH2:1]([N:8]1[CH2:13][C:12]2[N:14]=[C:15]([NH:31][CH2:30][C:29]3[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:28]=3[O:27][CH3:26])[CH:16]=[CH:17][C:11]=2[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 709805483-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

Product 1

HCID 709813623-benzyl-6-(2,4-dimethoxy-benzylamino)-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-oneYield 40.4%

Conditions

Temperature
150 °C

Procedure

A mixture of 3-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (112 mg, 0.34 mmol, 1.0 equiv) and 2,4-dimethoxybenzyl-amine (1.0 mL, 6.7 mmol, 20 equiv) was heated in the microwave reactor at 150° C. for 2 h. The crude reaction mixture was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-50%) to afford 3-benzyl-6-(2,4-dimethoxy-benzylamino)-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (66 mg). MS: [M+H]+=481.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-50%)

Sources & evidence

ORD record
ord-54764221af55409698c90b88316c6904
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

Loading…