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

HRID 1285150Notes

Reaction equation

HRID 1285150 reaction equation
O.[NH:2]1[C:10](=[O:11])[C:8](=[O:9])[C:6](=[O:7])[NH:5][C:3]1=[O:4].[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.Cl>C(O)C>[OH:9][C:8]1([C:14]2[N:13]([CH3:12])[CH:17]=[CH:16][CH:15]=2)[C:6](=[O:7])[NH:5][C:3](=[O:4])[NH:2][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73041-MethylpyrroleHCID 167232,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrate

Product 1

HCID 212712485-Hydroxy-5-(1-methyl-2-pyrrolyl)-2,4,6-(1H,3H,5H)pyrimidinetrioneYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alloxan hydrate (3.2 g., 0.02 mole) was dissolved in 50 ml. of ethanol by warming. 1-Methylpyrrole (1.6 g., 0.02 mole) was added and the mixture warmed for 5 minutes on a steam bath, while perfusing with hydrogen chloride. After standing at room temperature for 0.5 hour, the reaction mixture was evaporated to dryness and the residue triturated with water to yield title product as a solid [2.9 g.; m/e 223; Rf 0.5 (1:1 ethyl acetate:hexane/5% acetic acid)].

Workup

  1. temperaturethe mixture warmed for 5 minutes on a steam bath
  2. customthe reaction mixture was evaporated to dryness
  3. customthe residue triturated with water

Sources & evidence

ORD record
ord-37d5565ecd4d4c1396b7e5f4e45940ef
Source dataset
uspto-grants-1986_01
Patent number
US04565820

Reaction notes

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