Glycolic Acid → 2-Hydroxymethyl-3-methyl-5-phenylimidazo[5,4-b]pyridine

HRID 55543Notes

Reaction equation

HRID 55543 reaction equation
[NH2:1][C:2]1[C:3]([NH:14][CH3:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[C:16]([OH:20])(=O)[CH2:17]O>>[OH:20][CH2:16][C:17]1[N:14]([CH3:15])[C:3]2=[N:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:7]=[C:2]2[N:1]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 108456893-Amino-2-methylamino-6-phenylpyridine

Product 1

HCID 108475892-Hydroxymethyl-3-methyl-5-phenylimidazo[5,4-b]pyridineYield 15.3%

Procedure

A procedure similar to that described in Preparation 43 was repeated, except that 4.9 g of 3-amino-2-methylamino-6-phenylpyridine (prepared as described in Preparation 109) and 5.6 g of glycolic acid were used, and that the product was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of ethyl acetate and ethanol in ratios ranging from 1:0 to 10:1 by volume as the eluent, to give 0.9 g of the title compound, melting at 174°-177° 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. washa gradient elution method

Sources & evidence

ORD record
ord-fb5408ab5a8a4481ba4038554b03a6da
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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