Potassium Bicarbonate → HCID 86623407, compound

HRID 2111314Notes

Reaction equation

HRID 2111314 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH2:6][NH:7][CH:8]1[CH2:11][CH2:10][CH2:9]1)[CH3:2].[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=1.C(=O)(O)[O-].[K+]>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH2:6][N:7]([C:16]1[C:17]([N+:21]([O-:23])=[O:22])=[CH:18][N:19]=[C:14]([Cl:13])[N:15]=1)[CH:8]1[CH2:11][CH2:10][CH2:9]1)[CH3:2]

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57635029HCID 57635029, compound

Product 1

HCID 86623407HCID 86623407, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.9 g (0.011 mole) of 3-cyclobutylaminopropanoic acid ethyl ester in 7 mL of acetonitrile was added dropwise to a mixture of 1.74 g (0.09 mole) of 2,4-dichloro-5-nitro-pyrimidine and 2.07 g (0.021 mole) of potassium bicarbonate and 20 mL of acetonitrile at ambient temperature over 45 mins. The mixture was stirred for 2.5 hours, then diluted with 45 mL of ethyl acetate. The mixture was filtered, concentrated under reduced pressure and the residue purified by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-90:10) to give 1.7 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclobutyl-amino]-propanoic acid ethyl ester (IV-23).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe residue purified by silica gel chromatography
  4. washeluting with hexanes-ethyl acetate (100:0-90:10)

Sources & evidence

ORD record
ord-bc95350aad2a4c89a0c5f2ad1eb46c01
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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