(Rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2-methyl-propanoic acid methyl ester → (Rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2-methyl-propanoic acid methyl ester

HRID 2111271Notes

Reaction equation

HRID 2111271 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH3:22])[CH2:5][N:6]([C:12]1[C:17]([N+:18]([O-])=O)=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=1)[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH3:22])[CH2:5][N:6]([C:12]1[C:17]([NH2:18])=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=1)[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 58153870(Rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2-methyl-propanoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 87619052(Rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2-methyl-propanoic acid methyl esterYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 40.64 g (0.119 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2-methyl-propanoic acid methyl ester (IV-1) in 1500 mL of ethyl acetate and 14 g of 5% palladium on carbon catalyst was stirred under an atmosphere of hydrogen until hydrogen uptake was complete. The mixture was filtered through a pad of Celite, washing the filter pad with dichloromethane. Concentration under reduced pressure gave 35.2 g of (rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2-methyl-propanoic acid methyl ester (V-1), which also contained a small amount of (rac-)-2-chloro-9-cyclopentyl-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one. This material was used directly in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing the filter pad with dichloromethane
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-48cbff4bddd4457387c5e6f6b2e071f8
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

Loading…