Acetic Anhydride → 6-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-one

HRID 31065

Reaction equation

HRID 31065 reaction equation
[C:1](CC(O)=O)#[N:2].C(O[C:11](=[O:13])[CH3:12])(=O)C.[CH2:14]([NH:18][C:19]([NH:21][CH3:22])=[S:20])[CH:15]([CH3:17])[CH3:16].[OH-].[Na+]>C(O)C>[NH2:2][C:1]1[N:18]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:19](=[S:20])[N:21]([CH3:22])[C:11](=[O:13])[CH:12]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 14798Sodium HydroxideHCID 155682431-Isobutyl-3-methylthiourea

Product 1

HCID 866010566-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-oneYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of cyanoacetic acid (1.52 g, 17.8 mmol) in acetic anhydride (2.45 mL, 25.9 mmol) was added to 1-isobutyl-3-methylthiourea (2.37 g, 16.2 mmol). The reaction mixture was heated to 60° C. for 1.5 h. The solvent was evaporated and the resulting red oil was redissolved in ethanol (5 mL) and 5M sodium hydroxide (1.6 mL, 8.1 mmol) was added. The reaction mixture was refluxed for 2 h. The solvent was co-evaporated with ethanol and the resulting pale brown solid was purified by flash chromatography (ethyl acetate) to yield 6-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-one (1.0 g, 29%) as a yellow solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting red oil was redissolved in ethanol (5 mL)
  3. temperatureThe reaction mixture was refluxed for 2 h
  4. customthe resulting pale brown solid was purified by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1ed6a4e0efb34e3d84ef3149d73d0e7f
Source dataset
uspto-grants-2008_09
Patent number
US07425560B2

Linked notes

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