Hydrochloric Acid → Eniluracil

HRID 645343Notes

Reaction equation

HRID 645343 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, 24.4 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-c0b8c993915a4d509b9406c6a8eb3704
Source dataset
uspto-grants-2010_04
Patent number
US07704971B2

Reaction notes

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