Hydrochloric Acid → 5-Hydroxy-5-[1-(1-butyl)-2-pyrrolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

HRID 1285151

Reaction equation

HRID 1285151 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[K].I[CH2:8][CH2:9][CH2:10][CH3:11].[NH:12]1[C:20](=[O:21])[C:18](=[O:19])[C:16](=[O:17])[NH:15][C:13]1=[O:14].Cl>C(O)C.O1CCCC1>[OH:19][C:18]1([C:2]2[N:1]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][CH:3]=2)[C:16](=[O:17])[NH:15][C:13](=[O:14])[NH:12][C:20]1=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5781AlloxanHCID 10962Butyl iodideHCID 241923201H-Pyrrole, potassium salt (1:1)

Product 1

HCID 132828935-Hydroxy-5-[1-(1-butyl)-2-pyrrolyl)-2,4,6-(1H,3H,5H)pyrimidinetrioneYield 64.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium pyrrole (3.0 g., 0.03 mole), 1-iodobutane (9.2 g., 0.05 moles) and 10 ml. of tetrahydrofuran were combined and refluxed for 1.5 hours by which time the reaction mixture had become a thick mass. The reaction mixture was diluted with 30 ml. of water and extracted with 35 ml. of ether. The ether was backwashed with water, then added to a solution of anhydrous alloxan (4.8 g., 0.03 mole) obtained by heating in 50 ml. of ethanol. The ether was distilled away, 6N hydrochloric acid (5 ml., 0.03 mole) was added, and the mixture refluxed for 3 minutes, cooled, evaporated to a gum, and triturated with water to afford title product [5.1 g.; m.p. 135 (dec); m/e 265].

Workup

  1. temperaturerefluxed for 1.5 hours by which time the reaction mixture
  2. additionThe reaction mixture was diluted with 30 ml
  3. extractionof water and extracted with 35 ml
  4. customobtained
  5. temperatureby heating in 50 ml
  6. distillationThe ether was distilled away
  7. temperaturethe mixture refluxed for 3 minutes
  8. temperaturecooled
  9. customevaporated to a gum
  10. customtriturated with water

Sources & evidence

ORD record
ord-7a3c7f20eba045148278b3a13bd0ea97
Source dataset
uspto-grants-1986_01
Patent number
US04565820

Linked notes

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