Diethyl Carbonate → HCID 136009158, compound

HRID 2179100Notes

Reaction equation

HRID 2179100 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17].[C:19](=O)(OCC)[O:20]CC.[O-]CC.[Na+]>C(O)C>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][N:6]2[C:2]3[NH:1][C:19](=[O:20])[NH:18][C:16](=[O:17])[C:3]=3[N:4]=[N:5]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 339321HCID 339321, compoundHCID 2723922Sodium ethoxide

Product 1

HCID 136009158HCID 136009158, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-Amino-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxamide (example 1, step a) (7.59 g, 30.7 mmol), diethyl carbonate (4.72 g, 39.9 mmol) and sodium ethoxide (3.76 g, 55.3 mmol) in ethanol (97.1 mL) was heated to reflux overnight. The solid was filtered, washed with EtOH and dried to give 3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione (8.542 g, 15.6 mmol, 50.9% yield) which was used in the consecutive step without further purification. MS (m/e): 272.0 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe solid was filtered
  4. washwashed with EtOH
  5. customdried

Sources & evidence

ORD record
ord-bdcf23d658834349ab3c7347202fd0e3
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

Loading…