Glycolic Acid → 2-Hydroxymethyl-5-methoxy-3-methylimidazo[5,4-b]pyridine

HRID 1738248Notes

Reaction equation

HRID 1738248 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][CH3:11])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C(O)(=O)[CH2:13][OH:14].O.[C:18]1(C)C=CC=CC=1>>[OH:14][CH2:13][C:11]1[N:10]([CH3:18])[C:3]2[C:2]([N:1]=1)=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[N:4]=2

Participants

5

Reactant 4

HCID 757Glycolic AcidHCID 962WaterHCID 1140TolueneHCID 57437606-methoxy-2-N-methylpyridine-2,3-diamine

Product 1

HCID 108216002-Hydroxymethyl-5-methoxy-3-methylimidazo[5,4-b]pyridine

Procedure

A solution of 2.20 g of 3-amino-6-methoxy-2-methylaminopyridine (prepared as described in Preparation 68) and 3.30 g of glycolic acid in 40 ml of toluene was heated under reflux for 4 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 30:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 620 mg of the title compound, melting at 138-140° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionafter which it was extracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter which the solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and methanol as the eluent

Sources & evidence

ORD record
ord-d540869ba37d4ea3a0611a2d9f4c5963
Source dataset
uspto-grants-1999_10
Patent number
US05962470

Reaction notes

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