Hydrogen Bromide → HCID 12951525, compound

HRID 485656Notes

Reaction equation

HRID 485656 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11](=[S:14])[NH:12][CH:13]=2)=[CH:5][CH:4]=1.Br.[CH3:19]I>C(O)(=O)C>[OH:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11]([S:14][CH3:19])=[N:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 6328Methyl iodideHCID 129459725-(4-Methoxybenzyl)-2-thiouracil

Product 1

HCID 12951525HCID 12951525, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
35 °C

Procedure

5-(4-Methoxybenzyl)-2-thiouracil (105 g) was refluxed in glacial acetic acid (800 ml) and 48% aqueous hydrobromic acid (400 ml) for 3 hrs. The solution was cooled to ca. 35° C., methyl iodide (53 ml) was added and the solution was refluxed for a further 2 hours. The mixture was evaporated to dryness in vacuo and water (500 ml) added to the residue. Sodium hydroxide was added to raise the pH to ca. 5. The solid which formed was filtered off and recrystallised from ethanol giving 4-hydroxybenzyl-2-methylthio-4-pyrimidone (43.1 g) m.p. 243°-4° C.

Workup

  1. temperaturethe solution was refluxed for a further 2 hours
  2. customThe mixture was evaporated to dryness in vacuo and water (500 ml)
  3. additionadded to the residue
  4. additionSodium hydroxide was added
  5. temperatureto raise the pH to ca. 5
  6. customThe solid which formed
  7. filtrationwas filtered off
  8. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-c58893013c9f46ba91e92c714b94d691
Source dataset
uspto-grants-1985_08
Patent number
US04537891

Reaction notes

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