Butylamine → 4-butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

HRID 1576092Notes

Reaction equation

HRID 1576092 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](OCC)=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21]>O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:22][CH2:18][CH2:19][CH2:20][CH3:21])=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 14590535CID 14590535

Product 1

HCID 537827204-butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.35 g of 4-ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.1 mol) is treated with 2.2 g of butylamine (0.03 mol) at 90° for 1 hour. After this period the mixture is cooled, diluted with 20 ml of water and the white crystalline precipitate is filtered off. Recrystallization from diethyl ether yields 1.7 g of 4-butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (72%), m.p. 181°.

Workup

  1. temperatureAfter this period the mixture is cooled
  2. filtrationthe white crystalline precipitate is filtered off
  3. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-edfb4fdb0925476cb6ef15cadb85ec8e
Source dataset
uspto-grants-1976_09
Patent number
US03979399

Reaction notes

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