Formaldehyde → HCID 178463048, compound

HRID 329181Notes

Reaction equation

HRID 329181 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([OH:12])=[CH:8][C:9]=2[CH3:11])[N:4]([CH2:13][CH3:14])[N:3]=1.[CH2:15]=O.[ClH:17].[CH3:18][NH:19][CH3:20]>CN(C)C=O>[ClH:17].[CH3:18][N:19]([CH2:15][C:8]1[C:9]([CH3:11])=[C:10]2[C:2]([CH3:1])=[N:3][N:4]([CH2:13][CH3:14])[C:5]2=[N:6][C:7]=1[OH:12])[CH3:20]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 178463049HCID 178463049, compound

Product 1

HCID 178463048HCID 178463048, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 28.7 g. of 3,4-dimethyl-1-ethyl-1H-pyrazolo[3,4-b]pyridin-6-ol (0.15 mol.) in 1 1, of dimethylformamide is added 6.75 g. of paraformaldehyde (0.22 mol.) and 13.5 g. of dimethylamine hydrochloride (0.165 mol.) and the mixture is heated at 80° with stirring for 22 hours. Within two hours the starting compounds become dissolved and crystallization of 5-[(dimethylamino)methyl]-3,4-dimethyl-1-ethyl-1H-pyrazolo[3,4-b]pyridin-6-ol, hydrochloride (1:1) begins, increasing after cooling, yield 25.3 g. (59%), m.p. 291°-294°. A sample, recrystallized from dimethylformamide and dried at 140°, melts at 292°-295° (dec.).

Workup

  1. additionTo a suspension of 28.7 g
  2. dissolutionWithin two hours the starting compounds become dissolved
  3. customcrystallization of 5-[(dimethylamino)methyl]-3,4-dimethyl-1-ethyl-1H-pyrazolo[3,4-b]pyridin-6-ol, hydrochloride (1:1)
  4. temperatureincreasing
  5. temperatureafter cooling
  6. customA sample, recrystallized from dimethylformamide
  7. customdried at 140°

Sources & evidence

ORD record
ord-e0ed4641726e4a858f237031bddc27cf
Source dataset
uspto-grants-1977_04
Patent number
US04020072

Reaction notes

Loading…