5-(4-Formylphenyl)pyrimidine → {3-[(4-Pyrimidin-5-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester

HRID 2300508Notes

Reaction equation

HRID 2300508 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:18]1[CH:23]=[C:22]([C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=2)[CH:21]=[N:20][CH:19]=1>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:28][C:27]2[CH:26]=[CH:25][C:24]([C:22]3[CH:21]=[N:20][CH:19]=[N:18][CH:23]=3)=[CH:31][CH:30]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 38612125-(4-Formylphenyl)pyrimidineHCID 20758042t-Butyl [3-(aminomethyl)phenoxy]acetate

Product 1

HCID 54341424{3-[(4-Pyrimidin-5-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound of Step A was prepared from (3-aminomethyl-phenoxy)-acetic acid tert-butyl ester, of Preparation 20, and 4-pyrimidin-5-yl-benzaldehyde, of Preparation 26, using the method described in Example 3, Step A, except that the reaction time for imine formation was 1.5 h and no triethylamine was used. 1H NMR (400 MHz, CDCl3) δ 9.18 (s, 1H), 8.93 (s, 2H), 7.65 (m, 1H), 7.48 (m, 3H), 7.24 (m, 1H), 6.94 (m, 2H), 6.77 (d, 1H), 4.51 (s, 2H), 3.85 (s, 2H), 3.79 (s, 2H), 1.46 (s, 9H); MS 406 (M+1).

Sources & evidence

ORD record
ord-cd9e6bb9b123448c8dddbfea6d8a98aa
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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