Propionyl chloride → HCID 13231236, compound

HRID 2164450Notes

Reaction equation

HRID 2164450 reaction equation
[NH2:1][C:2]1[O:3][N:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH3:14].[C:15](Cl)(=[O:18])[CH2:16][CH3:17]>N1C=CC=CC=1>[CH3:12][N:8]1[C:9](=[O:11])[C:10]2=[C:2]([NH:1][C:15](=[O:18])[CH2:16][CH3:17])[O:3][N:4]=[C:5]2[N:6]([CH3:14])[C:7]1=[O:13]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 126779883-Amino-5,7-dimethyl[1,2]oxazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 13231236HCID 13231236, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

0.588 g of 3-amino-5,7-dimethyl-isoxazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione was dissolved in 15 ml of pyridine under heating. Then, 1.5 g of propionyl chloride was added to the solution, and the mixture was stirred at 80° C. for 4 hours. The solvent was removed from the reaction solution under reduced pressure. To the residue was added water, which was subjected to extraction with chloroform. The chloroform layer was taken and dried over anhydrous sodium sulfate and evaporated to dryness. The residue was chromatographed on a column of silica gel, and the column was eluted with chloroform:acetone:formic acid (20:1:0.1). The intended compound was recovered from the resultant eluate and recrystallized from isopropyl ether-acetone to give 0.345 g of colorless prisms, melting point: 150°-152° C.

Workup

  1. temperatureunder heating
  2. customThe solvent was removed from the reaction solution under reduced pressure
  3. additionTo the residue was added water, which
  4. extractionwas subjected to extraction with chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was chromatographed on a column of silica gel
  8. washthe column was eluted with chloroform:acetone:formic acid (20:1:0.1)
  9. customThe intended compound was recovered from the resultant eluate
  10. customrecrystallized from isopropyl ether-acetone

Sources & evidence

ORD record
ord-354ed4014d514048b66a9297376ed52e
Source dataset
uspto-grants-1985_03
Patent number
US04504662

Reaction notes

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