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Hydrochloric Acid → 4,6-Dihydroxy-2-oxo-5-(1-phenylethyl)-2,5-dihydropyrimidin-5-yl 2,2-dimethylpropanoate

HRID 1578587
Notes
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Reaction equation

HRID 1578587 reaction equation
[OH:1][C:2]1([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].N1C=CC=CC=1.Cl.[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>>[C:26]([O:1][C:2]1([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:3](=[O:10])[NH:4][C:5](=[O:9])[NH:6][C:7]1=[O:8])(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 54220390HCID 54220390, compound

Product 1

HCID 30435434,6-Dihydroxy-2-oxo-5-(1-phenylethyl)-2,5-dihydropyrimidin-5-yl 2,2-dimethylpropanoate

Conditions

Temperature
75 °C

Procedure

The amount of 5 g. of 5-hydroxy-5-(1-phenylethyl) barbituric acid, prepared following the procedure described in Belgian Pat. No. 775,117, was dissolved in a mixture of pivaloyl chloride (5 ml.) and 60 ml. pyridine. The mixture was heated at 75°C overnight, then cooled and poured into ice containing 60 ml. of concentrated hydrochloric acid. The product was extracted four times with ethyl acetate, and the combined extracts washed with saturated sodium chloride solution, sodium bicarbonate solution, dilute hydrochloric acid and sodium chloride solution. After drying over anhydrous sodium sulfate, solvent was removed by evaporation on a Buchi Rotovapor apparatus. The resulting product was purified by column chromatography (230 g. silica gel). Elution with 5% ethyl acetate in benzene solution followed by recrystallization from benzene provided 5-pivaloyloxy-5-(1-phenylethyl) barbituric acid, m.p. 205°-207°C.

Workup

  1. temperaturecooled
  2. extractionThe product was extracted four times with ethyl acetate
  3. washthe combined extracts washed with saturated sodium chloride solution, sodium bicarbonate solution, dilute hydrochloric acid and sodium chloride solution
  4. dry with materialAfter drying over anhydrous sodium sulfate, solvent
  5. customwas removed by evaporation on a Buchi Rotovapor apparatus
  6. customThe resulting product was purified by column chromatography (230 g. silica gel)
  7. washElution with 5% ethyl acetate in benzene solution
  8. customfollowed by recrystallization from benzene

Sources & evidence

ORD record
ord-a12bcd7d782847109f3b725239fe2df6
Source dataset
uspto-grants-1976_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03937830

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes