Methyl formate → HCID 13337060, compound

HRID 1462592Notes

Reaction equation

HRID 1462592 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=[C:10]1[N:15]([CH3:16])[C:14](=[O:17])[N:13]([CH3:18])[C:12](=[O:19])[C:11]1=[N:20]O)([OH:3])=[O:2].[CH:22](OC)=[O:23]>[Pt]=O.CO>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[N:15]([CH3:16])[C:14](=[O:17])[N:13]([CH3:18])[C:12](=[O:19])[C:11]=1[NH:20][CH:22]=[O:23])([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 7865Methyl formateHCID 178481575HCID 178481575, compound

Product 1

HCID 13337060HCID 13337060, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 15.8 g (0.05 mol) of the oxime (III), 200 ml of methanol, and 100 mg of platinum oxide was shaken under 4 atmospheres H2 for 15 minutes at room temperature. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure (35° C.) to give a red oil. Methyl formate (200 ml) was added and the resulting mixture refluxed under argon for 20 hours. It was then cooled in an ice bath and the white solid collected by filtration. Recrystillization from methanol gave 9.82 g (63% yield) of the formamido uracil (IV) as white crystals, mp 152°-153° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure (35° C.)
  3. customto give a red oil
  4. temperaturethe resulting mixture refluxed under argon for 20 hours
  5. temperatureIt was then cooled in an ice bath
  6. filtrationthe white solid collected by filtration

Sources & evidence

ORD record
ord-834a8833db1040e0898ef51ad1be791d
Source dataset
uspto-grants-1984_07
Patent number
US04460772

Reaction notes

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