Cornforth reagent → HCID 18382510, compound

HRID 2297600Notes

Reaction equation

HRID 2297600 reaction equation
[CH2:1]([N:8]1[C:12]2[C:13](=[O:24])[N:14]([CH2:22][CH3:23])[C:15]3[N:16]([N:17]=[C:18]([CH2:20][OH:21])[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([N:8]1[C:12]2[C:13](=[O:24])[N:14]([CH2:22][CH3:23])[C:15]3[N:16]([N:17]=[C:18]([CH:20]=[O:21])[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 15432861HCID 15432861, compound

Product 1

HCID 18382510HCID 18382510, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.3 g of 6-benzyl-7-cyclopentyl-4-ethyl-2-hydroxymethyl-imidazo[4,5-e]-s-triazolo[1,5-a]pyrimidin-5-one (for preparation see Synthesis Example I) are dissolved in 1.1 ml of dichloromethane and 0.45 g of pyridinium dichromate are added. The brown suspension obtained is stirred for about 24 hours at ambient temperature. The solvent is distilled off and the residue remaining is stirred with an ethyl acetate/cyclohexane mixture (2:1.5 ml). The clear, light yellow supernatant solution is filtered through silica gel. After the solvent has been distilled off, 0.15 g of the title compound are left in the form of a colourless resin.

Workup

  1. customThe brown suspension obtained
  2. distillationThe solvent is distilled off
  3. stirringthe residue remaining is stirred with an ethyl acetate/cyclohexane mixture (2:1.5 ml)
  4. filtrationThe clear, light yellow supernatant solution is filtered through silica gel
  5. distillationAfter the solvent has been distilled off
  6. wait0.15 g of the title compound are left in the form of a colourless resin

Sources & evidence

ORD record
ord-3d471cb6ba6547ea9d7c14bfb4d7f58b
Source dataset
uspto-grants-2002_12
Patent number
US06492377B1

Reaction notes

Loading…