Dimethylamine → 4-Dimethylamino-1,3-dimethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine

HRID 1764096Notes

Reaction equation

HRID 1764096 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]2[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:3]=12.[CH3:19][NH:20][CH3:21]>>[CH3:19][N:20]([CH3:21])[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]2[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:3]=12

Participants

3

Reactant 2

HCID 674DimethylamineHCID 227705064-chloro-1,3-dimethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 227704984-Dimethylamino-1,3-dimethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine

Procedure

15.5 gms. of 4-chloro-1,3-dimethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine (0.06 mol.) are added to 132 ml. of a solution of dimethylamine (40%). The reaction mixture is heated at 190°-200° C. for 16 hours in an autoclave and after cooling to room temperature is evaporated in vacuo. The residue is treated with water and extracted with ether. After evaporation of the extract, the 4-dimethylamino-1,3-dimethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine (15.6 gms. = 98%) is recrystallized from ligroin, m.p. 90°-91° C.

Workup

  1. temperatureThe reaction mixture is heated at 190°-200° C. for 16 hours in an autoclave
  2. customis evaporated in vacuo
  3. additionThe residue is treated with water
  4. extractionextracted with ether
  5. customAfter evaporation of the extract
  6. customthe 4-dimethylamino-1,3-dimethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine (15.6 gms. = 98%) is recrystallized from ligroin, m.p. 90°-91° C.

Sources & evidence

ORD record
ord-4264836c56804627b9e7643e4485dd31
Source dataset
uspto-grants-1978_09
Patent number
US04115394

Reaction notes

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