Benzyl [2-(4-{[(4-fluorophenyl)methyl]carbamoyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl]carbamate → 2-(2-Aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

HRID 1161932Notes

Reaction equation

HRID 1161932 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]([C:19]([NH:22]C(=O)OCC3C=CC=CC=3)([CH3:21])[CH3:20])[N:13]([CH3:18])[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1>[Pd]>[NH2:22][C:19]([C:12]1[N:13]([CH3:18])[C:14](=[O:17])[C:15]([OH:16])=[C:10]([C:8]([NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:34][CH:33]=2)=[O:9])[N:11]=1)([CH3:21])[CH3:20]

Participants

3

Reactant 1

HCID 54725153Benzyl [2-(4-{[(4-fluorophenyl)methyl]carbamoyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl]carbamate

Product 1

HCID 547218802-(2-Aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A methanolic solution of Benzyl 1-(4-{[(4-fluorobenzyl)amino]carbonyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-1-methylethylcarbamate was stirred over night under a hydrogen atmosphere in the presence of catalytic 10% Pd/C. Catalyst was then filtered off through celite, and the filtrate was concentrated. Product was obtained after trituration with ethyl ether.

Workup

  1. filtrationCatalyst was then filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. customProduct was obtained after trituration with ethyl ether

Sources & evidence

ORD record
ord-e66292f934814adfadc8b2a5f3ee1387
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

Loading…