Sodium ethoxide → HCID 58138254, compound

HRID 1967563Notes

Reaction equation

HRID 1967563 reaction equation
[CH2:1]1[CH:3]([C:4]([NH2:6])=[NH:5])[CH2:2]1.Cl.[CH2:8]([O:10][C:11](=[O:19])[C:12](=O)/[CH:13]=[CH:14]/OCC)[CH3:9].[O-]CC.[Na+]>C(O)C>[CH2:8]([O:10][C:11]([C:12]1[CH:13]=[CH:14][N:6]=[C:4]([CH:3]2[CH2:2][CH2:1]2)[N:5]=1)=[O:19])[CH3:9]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 2781916Cyclopropanecarboximidamide hydrochlorideHCID 64217883-Butenoic acid, 4-ethoxy-2-oxo-, ethyl ester

Product 1

HCID 58138254HCID 58138254, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reference: Riley, T. A.; Hennen, W. J.; Dalley, N. K.; Wilson, B. E.; J. Heterocyclic Chem., 1987, 24, 955-964. Heat a mixture of cyclopropylcarbamidine hydrochloride (2.05 g, 17 mmol), (E)-4-ethoxy-2-oxo-but-3-enoic acid ethyl ester (4.39 g, 25.5 mmol), ethanol (12 mL), and sodium ethoxide (1.16 g, 17 mmol) in a microwave at 140° C. for 20 min. Concentrate the reaction mixture under reduced pressure and partition the residue between ethyl acetate and brine. Separate the organic layer and concentrate under reduced pressure. Purify the residue by silica gel chromatography (10-30% ethyl acetate/hexane) to give 2-cyclopropyl-pyrimidine-4-carboxylic acid ethyl ester (1.5 g, 46%) as light yellow oil. MS (m/z): 193.0 (M+H)+.

Workup

  1. temperatureHeat
  2. concentrationConcentrate the reaction mixture under reduced pressure
  3. custompartition the residue between ethyl acetate and brine
  4. customSeparate the organic layer
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by silica gel chromatography (10-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9bb22e86d5c143c8babe6e5c28e3f728
Source dataset
uspto-grants-2013_04
Patent number
US08420654B2

Reaction notes

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