Glycolic Acid → (5-ethoxy-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

HRID 1953741Notes

Reaction equation

HRID 1953741 reaction equation
[NH2:1][C:2]1[C:3]([NH:11][CH3:12])=[N:4][C:5]([O:8][CH2:9][CH3:10])=[CH:6][CH:7]=1.[C:13]([OH:17])(=O)[CH2:14]O>>[CH2:9]([O:8][C:5]1[N:4]=[C:3]2[N:11]([CH3:12])[C:14]([CH2:13][OH:17])=[N:1][C:2]2=[CH:7][CH:6]=1)[CH3:10]

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 10583205HCID 10583205, compound

Product 1

HCID 10560253(5-ethoxy-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanolYield 62.2%

Procedure

A procedure similar to that described in Preparation 43 was repeated, except that 4.15 g 3-amino-6-ethoxy-2-methylaminopyridine (prepared as described in Preparation 97), and 5.66 g of glycolic acid were used, and that the product was purified by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 3.20 g of the title compound, melting at 161° C.

Workup

  1. customA procedure similar to that described in Preparation 43
  2. customthat the product was purified by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and methanol as the eluent

Sources & evidence

ORD record
ord-196fb2361a484945a5d4403c023da216
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

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