Acetyl chloride → HCID 21714057, compound

HRID 650248Notes

Reaction equation

HRID 650248 reaction equation
Cl.[CH2:2]([N:5]1[C:10](=[O:11])[C:9]([NH2:12])=[CH:8][N:7]=[C:6]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:3]=[CH2:4].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27].C(=O)(O)[O-].[Na+]>O1CCCC1>[C:26]([NH:12][C:9]1[C:10](=[O:11])[N:5]([CH2:2][CH:3]=[CH2:4])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][CH:8]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 21714063HCID 21714063, compound

Product 1

HCID 21714057HCID 21714057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Allyl-5-amino-6-oxo-2-phenyl-1,6-dihydropyrimidine hydrochloride was dissolved in tetrahydrofuran (27 ml) and triethylamine (1.16 ml, 8.33 mmol), and acetyl chloride (0.284 ml, 3.99 mmol) was added to it under cooling on ice, and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 2 hours. After saturated aqueous sodium bicarbonate was added, the reaction solution was extracted with ethyl acetate, and it was washed with saturated saline. After dried over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) whereby the title compound (617 mg, 69%) was obtained.

Workup

  1. temperatureunder cooling on ice
  2. extractionthe reaction solution was extracted with ethyl acetate, and it
  3. washwas washed with saturated saline
  4. dry with materialAfter dried over anhydrous sodium sulfate
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) whereby the title compound (617 mg, 69%)
  7. customwas obtained

Sources & evidence

ORD record
ord-a2747ea284f34f46b162a8d7a2a1ee09
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

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