Water → HCID 69300236, compound

HRID 886583Notes

Reaction equation

HRID 886583 reaction equation
[OH-:1].[Li+].C[O:4][C:5](=[O:39])[CH:6](O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[N:20][N:19]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:16]3=[N:17][CH:18]=2)[N:8]=1.O>O.CO>[OH:1][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]([OH:4])=[O:39])=[N:8][C:9]=1[C:13]1[CH:14]=[C:15]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[N:20][N:19]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:35])[CH3:36])[C:16]2=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59824934HCID 59824934, compound

Product 1

HCID 69300236HCID 69300236, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

4 N aqueous lithium hydroxide (17 μl, 0.66 mmol) was added to hydroxy-{6-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid methyl ester (286 mg, 0.55 mmol) in water/methanol(3:1) (5 ml) and stirred at room temperature for 3 days. Water was added and the mixture was extracted with ethyl acetate (3×), the combined organic layers were dried over magnesium sulfate and purified by silica gel chromatography to give 5-hydroxy-{6-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid (174 mg, 61% yield) as an off white powder. MS: m/z 507.6 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. dry with materialthe combined organic layers were dried over magnesium sulfate
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-bf18dd87cd1a4ba4ab34605995936a53
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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