Hydrochloric Acid → Eniluracil

HRID 1355553Notes

Reaction equation

HRID 1355553 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1)(C)C.C[O-].[Na+].Cl>CO>[C:6]([C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 127820375-((trimethylsilyl)ethynyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 43157Eniluracil

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-(trimethylsilylethynyl)uracil (5.3 g, 25.4 mmol) in 0.2M solution of sodium methoxide in methanol (400 mL) was stirred at room temperature for 3 hours and neutralized to pH 7 with dilute hydrochloric acid. The precipitated product was filtered, washed with methanol and dried to give a first crop of the title compound. The filtrates and washings were combined, evaporated to dryness and the residue crystallised from methanol to give the second crop of product. Combination of both crops and a further recrystallisation from ethanol gave a pure product.

Workup

  1. filtrationThe precipitated product was filtered
  2. washwashed with methanol
  3. customdried

Sources & evidence

ORD record
ord-6b9074385ab242339a43c023d251b36b
Source dataset
uspto-grants-2003_07
Patent number
US06586440B2

Reaction notes

Loading…