Potassium Hydroxide → HCID 13934569, compound

HRID 542661Notes

Reaction equation

HRID 542661 reaction equation
C([C:3](CC)(C([O-])=O)[C:4]([O-])=[O:5])C.[Na].[CH3:13][O:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[C:18]([CH:23]=[CH:24][C:25](=[O:27])[CH3:26])=[C:17]([O:28][CH3:29])[N:16]=1.[OH-].[K+]>C(O)C>[OH:5][C:4]1[CH2:3][CH:23]([C:18]2[C:19]([O:21][CH3:22])=[N:20][C:15]([O:14][CH3:13])=[N:16][C:17]=2[O:28][CH3:29])[CH2:24][C:25](=[O:27])[CH:26]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 5360545SodiumHCID 69515632,2-DiethylpropanedioateHCID 53729464HCID 53729464, compound

Product 1

HCID 13934569HCID 13934569, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Diethylmalonate (4.5 g) was added to a solution of sodium metal (0.65 g) in absolute ethanol (30 ml) and the mixture was heated under reflux with stirring. 1-(2,4,6-Trimethoxy-5-pyrimidylbut-1-en-3-one (6.4 g) was added and the mixture was then boiled under reflux for 2 hours. An aqueous solution of potassium hydroxide (3.5 g in 80 ml of water) was added and the mixture was heated under reflux for a further 5 hours. The solution was cooled and extracted with chloroform (50 ml) and then the aqueous layer was heated to 90° C. and carefully acidified (pH 4.5) with dilute aqueous hydrochloric acid. The resultant precipitate was removed by filtration to give 3-hydroxy-5-(2,4,6-trimethoxy-5-pyrimidyl)cyclohex-2-en-1-one (5.2 g) as a pale yellow crystalline solid, mp 215° C. (dec). Extraction of the filtrate with ethylacetate gave a further 0.7 g of product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureunder reflux for 2 hours
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a further 5 hours
  6. temperatureThe solution was cooled
  7. extractionextracted with chloroform (50 ml)
  8. customThe resultant precipitate was removed by filtration

Sources & evidence

ORD record
ord-26a9840fe5b544479db741df8da81939
Source dataset
uspto-grants-1987_04
Patent number
US04659362

Reaction notes

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