Formaldehyde → 6-Dimethylamino-3-methyl-1-(2-pyridinyl)-1,9-dihydro-4h-pyrazolo[3,4-b]quinolin-4-one

HRID 498031Notes

Reaction equation

HRID 498031 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:6]=1[C:5]2=[O:22].[B-][C:24]#[N:25].[Na+].[CH2:27]=O>C(O)(=O)C>[CH3:27][N:25]([CH3:24])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:6]=1[C:5]2=[O:22]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 20587905Sodium cyanoborohydride [MI]HCID 1358480556-Amino-3-methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

Product 1

HCID 1358480686-Dimethylamino-3-methyl-1-(2-pyridinyl)-1,9-dihydro-4h-pyrazolo[3,4-b]quinolin-4-oneYield 51.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-amino-3-methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one (1.00 g, 3.43 mmol), sodium cyanotrihydroborate (1.08 g, 17.2 mmol) and paraformaldehyde (1.00 g) in acetic acid (20 mL) was stirred at room temperature for 18 hours under an argon atmosphere. The reaction solvent was evaporated under reduced pressure, and the residue was poured into iced water. After the solution was made basic by the addition of a sodium hydroxide solution, the organic matter was extracted with chloroform. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform to chloroform:methanol=99:1) to give the title compound (0.56 g, 51% yield).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure
  2. additionthe residue was poured into iced water
  3. additionAfter the solution was made basic by the addition of a sodium hydroxide solution
  4. extractionthe organic matter was extracted with chloroform
  5. washThe extract was washed with saturated brine and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (chloroform to chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-2baf92de339743ee80e86932a5301bbd
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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