5-Ethoxycarbonylmethyl-2-methyl-3-(1-phenyl-cyclopentylmethyl)-2,5-dihydro-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester → 5-Hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

HRID 1409560Notes

Reaction equation

HRID 1409560 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:24][C:25]([O:27]CC)=O)O[N:9]([CH3:11])[C:8]([CH2:12][C:13]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:7]1)=[O:5])[CH3:2].C[O:31]C(C1N=C(CC2(C3C=CC=CC=3)CCCC2)NC(=O)C=1O)=O>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:12][C:13]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:15][CH2:16][CH2:17]2)[N:9]([CH3:11])[C:25](=[O:27])[C:24]=1[OH:31])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 867102615-Ethoxycarbonylmethyl-2-methyl-3-(1-phenyl-cyclopentylmethyl)-2,5-dihydro-[1,2,4]oxadiazole-5-carboxylic acid ethyl esterHCID 136377077Methyl 5,6-dihydroxy-2-((1-phenylcyclopentyl)methyl)pyrimidine-4-carboxylate

Product 1

HCID 867102605-Hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Procedure

5-Hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester was synthesized as a brown solid (35 mg, 20%) from 200 mg of 5-ethoxycarbonylmethyl-2-methyl-3-(1-phenyl-cyclopentylmethyl)-2,5-dihydro-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester following the procedure described for 5-hydroxy-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (Example 6). LCMS: m/z=357.0 (MH+).

Sources & evidence

ORD record
ord-a528acfcb7ad41e1a3159ac8a6da45c0
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

Loading…