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

HRID 1599305ノート

反応式

HRID 1599305 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-360787e783f54c4dbacb8983cfc68c39
出典データセット
uspto-grants-1998_04
特許番号
US05739345

反応ノート

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