Alloxan → HCID 12962671, compound

HRID 1262935Notes

Reaction equation

HRID 1262935 reaction equation
COC1SC=CC=1.[OH:8][C:9]1([C:18]2[S:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]1=[O:17].C([Li])CCC.CCCCCC.N1C(=O)C(=O)C(=O)NC1=O>O1CCCC1.CCOCC>[OH:8][C:9]1([C:18]2[S:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:10](=[O:17])[NH:11][C:12](=[O:16])[NH:13][C:14]1=[O:15]

Participants

7

Reactant 4

HCID 5781AlloxanHCID 8058HexaneHCID 20456473HCID 20456473, compoundHCID 178418339Butyllithium

Product 1

HCID 12962671HCID 12962671, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Hydroxy-5-(5-methoxy-2-thienyl)-2,4,6(1H,3H,5H)-pyrimidinetrione 2-Methoxythiophene (2.3 g., 20 mmoles) was dissolved in 35 ml. of ether. With cooling, butyl lithium in hexane (2.4 M, 9 ml., 21.6 mmoles) was added dropwise over 15 minutes, the temperature rising as high as 35° C. during this addition. The reaction mixture was stirred for 1 hour at room temperature. While maintaining the temperature between -20° and -15° C., sublimed alloxan (3 g., 21 mmoles) in 20 ml. of tetrahydrofuran was added during 10 minutes. The mixture was warmed to room temperature, stirred for 0.5 hour, cooled to 5° C. and quenched by adding 35 ml. of 1 N hydrochloric acid in portions. The organic phase was separated and the aqueous phase extracted with 25 ml. of ethyl acetate. The combined organic phase and extract were back-washed with water, concentrated to dryness and triturated with hexane to yield solid 5-hydroxy-5-(5-methoxy-2-thienyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (1.4 g., m/e 256).

Workup

  1. temperatureWith cooling
  2. additionthe temperature rising as high as 35° C. during this addition
  3. temperatureThe mixture was warmed to room temperature
  4. stirringstirred for 0.5 hour
  5. temperaturecooled to 5° C.
  6. customquenched
  7. additionby adding 35 ml
  8. customThe organic phase was separated
  9. extractionthe aqueous phase extracted with 25 ml
  10. extractionThe combined organic phase and extract
  11. washwere back-washed with water
  12. concentrationconcentrated to dryness
  13. customtriturated with hexane

Sources & evidence

ORD record
ord-afa627af87114163b278e449bdc8396b
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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