2,2-Dimethoxypropane → HCID 20038761, compound

HRID 1904262Notes

Reaction equation

HRID 1904262 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:8]=[C:7]2[CH:16]=[N:17][NH:18][C:6]=12)[CH:2]=[CH2:3].[CH3:19][O:20][C:21](OC)([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([NH:4][C:5]1[C:6]2[C:7](=[CH:16][N:17]([C:21]([O:20][CH3:19])([CH3:23])[CH3:22])[N:18]=2)[N:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 11430Potassium CarbonateHCID 13747174HCID 13747174, compound

Product 1

HCID 20038761HCID 20038761, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 180AcetoneSolvent

Procedure

A mixture of ethyl 7-allylamino-1H-pyrazolo[4,3-b]-pyridine-6-carboxylate (3.69 g, 15 mmol), 2,2-dimethoxypropane (9.2 ml, 75 mmol) and 4-toluenesulphonic acid (142 mg, 0.75 mmol) in acetone (200 ml) was heated under reflux for 48 h. The solution was cooled and stirred with solid potassium carbonate, then filtered and evaporated in vacuo. Column chromatography of the residue on basic alumina (100 g), eluting with ethyl acetate, gave the title compound as a white solid (3.07 g, 64%), m.p. 102°-103° C. Found: C, 60.31; H, 6.78; N, 17.60; C16H22N4O3 requires C, 60.36; H, 6.97; N, 17.60%

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. washColumn chromatography of the residue on basic alumina (100 g), eluting with ethyl acetate

Sources & evidence

ORD record
ord-a1dcdd14b4794693bddd5929abe77e02
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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