Potassium Carbonate → HCID 21421722, compound

HRID 259404Notes

Reaction equation

HRID 259404 reaction equation
[OH:1][C:2]1[C:3]2[C:4](=[N:16][N:17]([CH3:19])[CH:18]=2)[N:5]=[CH:6][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].[CH3:20][N:21]([CH2:23][CH2:24][CH2:25]Cl)[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:8]([C:7]1[C:2](=[O:1])[C:3]2[C:4](=[N:16][N:17]([CH3:19])[CH:18]=2)[N:5]([CH2:25][CH2:24][CH2:23][N:21]([CH3:22])[CH3:20])[CH:6]=1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 178479973HCID 178479973, compound

Product 1

HCID 21421722HCID 21421722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.1 g. of (4-hydroxy-2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)phenylmethanone (0.02 mol.), 4.8 g. of dimethylaminopropyl chloride (0.04 mol.) and 5.6 g. of potassium carbonate (0.04 mol.) are heated in 50 ml. of dimethylformamide at 80° for 12 hours with stirring. The mixture is filtered hot, evaporated to dryness and the residue is recrystallized from ethyl acetate to obtain 5-benzoyl-7-[3-(dimethylamino)Propyl]-2,7-dihydro-2-methyl-4H-pyrazolo[3,4-b]pyridin-4-one, yield 4.6 g. (68%); m.p. 186°-188°.

Workup

  1. filtrationThe mixture is filtered hot
  2. customevaporated to dryness
  3. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7c7bb30519ab4062a6db1c1eb95395ce
Source dataset
uspto-grants-1977_07
Patent number
US04038281

Reaction notes

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