5-(4-Formylphenyl)pyrimidine → 3-{3-[(4-Pyrimidin-5-yl-benzylamino)-methyl]-phenyl}propionic acid methyl ester

HRID 2300456Notes

Reaction equation

HRID 2300456 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH2:14])[CH:8]=1.[N:16]1[CH:21]=[C:20]([C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=2)[CH:19]=[N:18][CH:17]=1>CO>[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH:14][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:20]3[CH:19]=[N:18][CH:17]=[N:16][CH:21]=3)=[CH:29][CH:28]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 38612125-(4-Formylphenyl)pyrimidineHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 542194583-{3-[(4-Pyrimidin-5-yl-benzylamino)-methyl]-phenyl}propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Step A was prepared from 3-(3-aminomethyl--phenyl)-propionic acid methyl ester hydrochloride salt, of Preparation 44, and 4-pyrimidin-5-yl-benzaldehyde, of Preparation 26, using the method described in Example 1, Step A except the imine was formed in MeOH at reflux over 2 h. 1H NMR (400 MHz, CDCl3)δ 9.19 (s, 1H), 8.92 (s, 2H), 7.55 (m, 4H), 7.25 (m, 3H), 7.11 (d, 1H), 3.87 (s, 2H), 3.81 (s, 2H), 3.66 (s, 3H), 2.95 (t, 2H), 2.63 (t, 2H); MS 362 (M+1).

Workup

  1. temperatureat reflux over 2 h

Sources & evidence

ORD record
ord-3838317a3278477eb80c8337ca21dc20
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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