Dimethyl Sulfoxide → 1,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1456031Notes

Reaction equation

HRID 1456031 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]3[C:13]([C:14](Cl)=[C:5]2[C:4]([CH3:16])=[N:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CS(C)=O>O>[CH3:1][N:2]1[C:6]2=[N:7][C:8]3[C:13]([C:14]([NH:24][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:5]2[C:4]([CH3:16])=[N:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7504BenzylamineHCID 134489994-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 195922281,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,3-dimethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.2 g, 0.005 mol), benzylamine (1.2 ml) and DMSO (3 ml) was heated at 80°-90° C. for 3-4 hours. The reaction mixture was cooled to room temperature and then was poured into water. The mixture was extracted with CH2C2 (3×50 ml) and then the CH2Cl2 layers were combined and evaporated. The residue was purified by column chromatography on silca gel eluting with ethyl acetate to afford the product which was crystallized from ether/hexane to afford 1.2 g of 1,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid, m.p. 105° C.

Workup

  1. temperaturewas heated at 80°-90° C. for 3-4 hours
  2. extractionThe mixture was extracted with CH2C2 (3×50 ml)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silca gel
  5. washeluting with ethyl acetate
  6. customto afford the product which
  7. customwas crystallized from ether/hexane

Sources & evidence

ORD record
ord-d8c97f724afa48a4a42c9217ca121398
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

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