Sodium Hydroxide → HCID 21537702, compound

HRID 1076554Notes

Reaction equation

HRID 1076554 reaction equation
C(N[C:6]([C:8]1[N:9]=[C:10]2[CH:21]=[N:20][N:19]([CH2:22][CH3:23])[C:11]2=[N:12][C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:7])CCC.[OH-:24].[Na+]>C(O)C>[CH2:15]([NH:14][C:13]1[N:12]=[C:11]2[N:19]([CH2:22][CH3:23])[N:20]=[CH:21][C:10]2=[N:9][C:8]=1[C:6]([OH:7])=[O:24])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21537694HCID 21537694, compound

Product 1

HCID 21537702HCID 21537702, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23.5 g. of N-butyl-6-butylamino-1-ethyl-1H-pyrazolo-[3,4-b]pyrazine-5-carboxamide (0.0735 mol.) suspended in 230 ml. of sodium hydroxide (2.5 N) and 460 ml. of ethanol are heated at reflux for 48 hours. Then the solution is evaporated to a volume of about 60-80 ml. The sodium salt of the acid precipitates. Acidification of the pulp with dilute hydrochloric acid with stirring provides 6-butylamino-1-ethyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid which is filtered off, washed with water and dried at 75°, yield 17.7 g. (91%), m.p., 97°-98° (hexane). The ester is prepared by reacting the foregoing acid with alcoholic hydrochloric acid at room temperature for 4 days. After this period, the ethanol is evaporated, the residue treated with dilute ammonia in order to remove unreacted acid and then dried at 40°. Recrystallization from ligroin yields 6-butylamino-1-ethyl-1H-pyrazolo[3,4-b]-pyrazine-5-carboxylic acid ethyl ester, m.p. 64.5°-65.5°.

Workup

  1. temperatureat reflux for 48 hours
  2. customThen the solution is evaporated to a volume of about 60-80 ml
  3. customThe sodium salt of the acid precipitates

Sources & evidence

ORD record
ord-f3def5fe32d14f94a90e8f6e432407e3
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

Loading…