1-{[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl ester → 1-{[(5-Amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl ester

HRID 2111382Notes

Reaction equation

HRID 2111382 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:8][N:9]([C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][N:18]=[C:17]([Cl:24])[N:16]=2)[CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:7][CH2:6]1)=[O:4]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1([CH2:8][N:9]([C:15]2[C:20]([NH2:21])=[CH:19][N:18]=[C:17]([Cl:24])[N:16]=2)[CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:7]1)=[O:4]

Participants

4

Reactant 1

HCID 579700121-{[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 866234201-{[(5-Amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.20 g (0.00679 mole) of 1-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl ester (IV-53), 0.75 g of 5% palladium on carbon catalyst, and 80 mL of ethyl acetate was stirred under an atmosphere of hydrogen until the reaction was complete. The resulting mixture was filtered through Celite and the combined filtrate was concentrated under reduced pressure to give 1.94 g of 1-{[(5-amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl ester (V-53) as an off-white solid.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. concentrationthe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6efaf033bcaf4328bb5c3620f46d3ade
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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