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

HRID 1458746Notes

Reaction equation

HRID 1458746 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) is heated at 80°-90° C. for 3-4 hours. The reaction mixture is cooled to room temperature and then is poured into water. The mixture is extracted with CH2Cl2 (3×50 ml) and then the CH2Cl2 layers are combined and evaporated. The residue is purified by column chromatography on silca gel eluting with ethyl acetate to afford the product which is 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. temperatureis heated at 80°-90° C. for 3-4 hours
  2. extractionThe mixture is extracted with CH2Cl2 (3×50 ml)
  3. customevaporated
  4. customThe residue is purified by column chromatography on silca gel
  5. washeluting with ethyl acetate
  6. customto afford the product which
  7. customis crystallized from ether/hexane

Sources & evidence

ORD record
ord-bf4a9ffa37e146488e0d4ec81e0d436c
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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