Methanol → 9-butyl-3-(methoxymethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 1664523Notes

Reaction equation

HRID 1664523 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][NH:10][C:9]=2[C:8](=[O:14])[N:7]2[C:15]([CH2:18]Cl)=[N:16][N:17]=[C:6]12)[CH2:2][CH2:3][CH3:4].[CH3:20][OH:21]>C[O-].[Na+].O>[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][NH:10][C:9]=2[C:8](=[O:14])[N:7]2[C:15]([CH2:18][O:21][CH3:20])=[N:16][N:17]=[C:6]12)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 887MethanolHCID 667256359-Butyl-3-(chloromethyl)-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one

Product 1

HCID 667255489-butyl-3-(methoxymethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-oneYield 17.42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10942334Sodium MethoxideSolvent

Procedure

The mixture of 9-butyl-3-(chloromethyl)-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (35 mg, 125 mmol) in 4 M of sodium methoxide in methanol (0.5 mL, 2 mmol) was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The combined organic layers was dried with sodium sulfate, filtered, and concentrated in vacuo to yield the desired product (6 mg, 17.42%). LCMS calculated for C13H19N6O2 (M+H): 290.2. found 290.2.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic layers was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c61ed5224c84c01a6fec8462948e91a
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

Loading…