2-hydroxymethyl-6-nitro-3-methyl-3H-imidazo[4,5-b]pyridine → (6-Amino-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

HRID 1911238Notes

Reaction equation

HRID 1911238 reaction equation
[OH:1][CH2:2][C:3]1[N:14]([CH3:15])[C:6]2=[N:7][CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=[C:5]2[N:4]=1.[H][H]>[Pd]>[NH2:11][C:9]1[CH:10]=[C:5]2[N:4]=[C:3]([CH2:2][OH:1])[N:14]([CH3:15])[C:6]2=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 668880462-hydroxymethyl-6-nitro-3-methyl-3H-imidazo[4,5-b]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 66888727(6-Amino-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanolYield 0.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 0.5 g (2.4 mol) of 2-hydroxymethyl-6-nitro-3-methyl-3H-imidazo[4,5-b]pyridine, prepared in the preceding step, and 0.3 g of 10% palladium-on-charcoal is stirred for 3 hours under 2.5 atm. of hydrogen. After this time, the suspension is filtered through a pad of Celite and the filtrate is concentrated under reduced pressure. 0.4 g of the expected product is thus isolated, and is used without further purification in the rest of the synthesis.

Workup

  1. filtrationAfter this time, the suspension is filtered through a pad of Celite
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5fb678b4d87c4eb7b6eec2a815e62c02
Source dataset
uspto-grants-2013_12
Patent number
US08604050B2

Reaction notes

Loading…