Potassium Bicarbonate → HCID 87617703, compound

HRID 2111369Notes

Reaction equation

HRID 2111369 reaction equation
[CH:1]1([NH:6][CH2:7][CH:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1.C(=O)(O)[O-].[K+]>C(OCC)C.O>[Cl:14][C:15]1[N:20]=[C:19]([N:6]([CH2:7][CH:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57635054HCID 57635054, compound

Product 1

HCID 87617703HCID 87617703, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.67 g (0.009 mole) of 3-cyclopentylaminomethyl-dihydro-furan-2-one in 25 mL of ethyl ether was added 15 mL of ice-water followed by 1.68 g (0.0087 mole) of 2,4-dichloro-5-nitro-pyrimidine. A solution of 1.36 g (0.014 mole) of potassium bicarbonate in 5 mL of water was added over 20 minutes. The mixture was stirred overnight at ambient temperature. The mixture was concentrated under reduced pressure to remove the ethyl ether and the mixture then filtered, washing with water and then water-acetonitrile. The solid was purified by recrystallization from hexanes-ethyl acetate (1:1) to give 2.2 g of (rac)-3-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-dihydro-furan-2-one (IV-49).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove the ethyl ether
  3. filtrationthe mixture then filtered
  4. washwashing with water
  5. customThe solid was purified by recrystallization from hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7ee7670b421f4fb988febdfd60921fbb
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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