Ethylorthoformate → 9-Benzyl-6-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[3,4-i]purin-5-one

HRID 249766Notes

Reaction equation

HRID 249766 reaction equation
[CH2:1]([N:8]1[C:16]2/[C:15](=[N:17]/[NH2:18])/[NH:14][C:13](=[O:19])[N:12]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]([O-])([O-])OCC>>[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][N:18]=[CH:25][N:14]3[C:13](=[O:19])[N:12]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 53630039EthylorthoformateHCID 178446229HCID 178446229, compound

Product 1

HCID 598538329-Benzyl-6-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[3,4-i]purin-5-oneYield 49.5%

Conditions

Temperature
60 °C

Procedure

(6Z)-7-Benzyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 6-hydrazone (0.50 g, 1.5 mmol) was mixed with ethyl orthoformate (5 mL, 30 mmol). After being stirred at 60° C. for 1 h, the reaction mixture was concentrated in vacuum. The residue was treated with ether to yield the desired product as a white solid (0.25 g, 48.5%). LCMS calculated for C18H21N6O (M+H): 337.2. found: 337.1.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuum
  2. additionThe residue was treated with ether

Sources & evidence

ORD record
ord-e4096b53239f4892a4aea6a90513002c
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

Loading…