Methyl formate → HCID 13337060, compound

HRID 365064Notes

Reaction equation

HRID 365064 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 887MethanolSolvent

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. Recrystallization 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
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-788d5d61e5d647f2b8ac8014e415c5fe
Source dataset
uspto-grants-1986_08
Patent number
US04608336

Reaction notes

Loading…