Potassium Hydroxide → 2-Benzyloxymethyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

HRID 57722Notes

Reaction equation

HRID 57722 reaction equation
[OH-].[K+].[CH2:3]([O:10][CH2:11][C:12]([NH:14][N:15]1[C:19]([C:20]([NH2:22])=[O:21])=[CH:18][N:17]=[CH:16]1)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.CCO>[CH2:3]([O:10][CH2:11][C:12]1[NH:22][C:20](=[O:21])[C:19]2=[CH:18][N:17]=[CH:16][N:15]2[N:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 897148121-[[2-(Phenylmethoxy)acetyl]amino]-1H-imidazole-5-carboxamide

Product 1

HCID 1365928012-Benzyloxymethyl-3H-imidazo[5,1-f][1,2,4]triazin-4-oneYield 71.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A solution of KOH (4.4 g, 78.5 mmol) in water (50 mL) was added dropwise to a solution of compound 3 (7.3 g, 26.6 mmol) in EtOH (60 mL) at room temperature. The resulting solution was heated to 110° C. for 3 hours. After removal of the organic solvent, the mixture was poured into ice water and the pH was adjusted to 7.0 with 1M aqueous HCl solution. The suspension was filtered and the filtrate was dried to afford compound 4 (4.9 g, 71% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.05 (s, 1H), 8.45 (s, 1H), 7.74 (s, 1H), 7.39˜7.29 (m, 5H), 4.59 (s, 2H), 4.36 (s, 2H). LC-MS: m/z 257.2 [M+H]+.

Workup

  1. customAfter removal of the organic solvent
  2. additionthe mixture was poured into ice water
  3. filtrationThe suspension was filtered
  4. customthe filtrate was dried

Sources & evidence

ORD record
ord-bd29fcaf3967415291649e417f9726a5
Source dataset
uspto-grants-2016_09
Patent number
US09434733B2

Reaction notes

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