Furfurylamine → HCID 28905833, compound

HRID 2192770Notes

Reaction equation

HRID 2192770 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH2:15]([NH2:21])[C:16]1[O:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>CC(O)C>[O:20]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:15][NH:21][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1

Participants

6

Reactant 4

HCID 3438FurfurylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 28905833HCID 28905833, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (1.71 g) in 2-propanol (10 ml) were added furfurylamine (714 mg) and diisopropylethylamine (950 mg), and the mixture was stirred at room temperature for 10 min. The reaction mixture was poured into 2% aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and the precipitate was collected by filtration. The precipitate was dissolved in ethanol (10 ml), 2 M aqueous sodium hydroxide solution (10 ml) was added and the mixture was stirred at room temperature for 5 hr. The reaction mixture was adjusted to pH 3 with 1 M hydrochloric acid, and the precipitated crystals were collected by filtration to give the object compound (1.75 g) as a powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. filtrationthe precipitate was collected by filtration
  6. dissolutionThe precipitate was dissolved in ethanol (10 ml)
  7. addition2 M aqueous sodium hydroxide solution (10 ml) was added
  8. stirringthe mixture was stirred at room temperature for 5 hr
  9. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9f2a77065a3e4b48af5d1b5eb6961ab3
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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