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

HRID 2111381Notes

Reaction equation

HRID 2111381 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:8][NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:7][CH2:6]1)=[O:4].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1.O.C(=O)(O)[O-].[K+]>CCOCC>[CH3:1][O:2][C:3]([C:5]1([CH2:8][N:9]([C:18]2[C:19]([N+:23]([O-:25])=[O:24])=[CH:20][N:21]=[C:16]([Cl:15])[N:17]=2)[CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57635047HCID 57635047, compound

Product 1

HCID 579700121-{[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl esterYield 95.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4.88 g (0.0247 mole) of 1-cyclopentylaminomethyl-cyclopropanecarboxylic acid methyl ester and 4.48 g (0.0231 mole) of 2,4-dichloro-5-nitro-pyrimidine in 100 mL of ether was added 50 mL of water and 4.62 g (0.0462 mole) of potassium bicarbonate. The mixture was stirred at ambient temperature for 5 hours. The resulting two-layer mixture was separated and the aqueous layer was extracted with ether. The combined ether extracts were washed successively with aqueous sodium carbonate and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 7.80 g of 1-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclopropanecarboxylic acid methyl ester (IV-53) as a yellow solid.

Workup

  1. customThe resulting two-layer mixture was separated
  2. extractionthe aqueous layer was extracted with ether
  3. washThe combined ether extracts were washed successively with aqueous sodium carbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a03442062e5c4262bca30131a410da9f
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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