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

HRID 2117555Notes

Reaction equation

HRID 2117555 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 hand 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-7b2f272ef34544fc954137ed44d4f626
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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