2-Benzyloxymethyl-7-(3,6-dihydro-2H-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one → 2-Hydroxymethyl-7-(tetrahydro-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one

HRID 57725Notes

Reaction equation

HRID 57725 reaction equation
C([O:8][CH2:9][C:10]1[NH:15][C:14](=[O:16])[C:13]2=[CH:17][N:18]=[C:19]([C:20]3[CH2:21][CH2:22][O:23][CH2:24][CH:25]=3)[N:12]2[N:11]=1)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[OH:8][CH2:9][C:10]1[NH:15][C:14](=[O:16])[C:13]2=[CH:17][N:18]=[C:19]([CH:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[N:12]2[N:11]=1

Participants

5

Reactant 2

HCID 1370030512-Benzyloxymethyl-7-(3,6-dihydro-2H-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1365927412-Hydroxymethyl-7-(tetrahydro-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-oneYield 143.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 6 (650 mg, 1.14 mmol) in MeOH (30 mL) was added Pd(OH)2/C (120 mg). The reaction mixture was stirred under 50 psi of hydrogen at 70° C. until LC-MS showed that the starting material was almost consumed. The suspension was filtered through celite and washed with MeOH (20 mL×2) and the filtrate was concentrated in vacuo to afford compound 7 (410 mg, 85% yield) as a white solid. LC-MS: m/z 251.3 [M+H]+.

Workup

  1. customwas almost consumed
  2. filtrationThe suspension was filtered through celite
  3. washwashed with MeOH (20 mL×2)
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-807a570a88a7498d90dc59c661b68411
Source dataset
uspto-grants-2016_09
Patent number
US09434733B2

Reaction notes

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