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 2114792Notes

Reaction equation

HRID 2114792 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-500ad4a5164c46b587065131bb0dbaae
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

Loading…