Diethyl Ether → 3-[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl ester

HRID 2111328Notes

Reaction equation

HRID 2111328 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([CH3:13])([CH3:12])[CH2:5][NH:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1.CCOCC.C(=O)(O)[O-].[K+]>O>[CH3:1][O:2][C:3](=[O:14])[C:4]([CH3:12])([CH3:13])[CH2:5][N:6]([C:18]1[C:19]([N+:23]([O-:25])=[O:24])=[CH:20][N:21]=[C:16]([Cl:15])[N:17]=1)[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 576350433-Cyclopentylamino-2,2-dimethyl-propanoic acid methyl ester

Product 1

HCID 866234093-[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl esterYield 96.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5.02 g (0.025 mole) of 3-cyclopentylamino-2,2-dimethyl-propanoic acid methyl ester, 5.30 g (0.0276 mole) of 2,4-dichloro-5-nitro-pyrimidine and 100 mL of ether was added 20 mL of water and 5.00 g (0.050 mole) of potassium bicarbonate. The mixture was stirred at room temperature for 14 hours. The resulting two-layer mixture was separated and the aqueous layer was extracted twice with 20 mL of ether. The combined ether extracts were washed successively with 20 mL of aqueous sodium carbonate, twice with 20 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 8.60 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl ester (IV-38) as a yellow solid.

Workup

  1. customThe resulting two-layer mixture was separated
  2. extractionthe aqueous layer was extracted twice with 20 mL of ether
  3. washThe combined ether extracts were washed successively with 20 mL of aqueous sodium carbonate, twice with 20 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88e9254c57fb455aa7297634833f6d29
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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