Water → HCID 20038774, compound

HRID 1904263Notes

Reaction equation

HRID 1904263 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[C:7](=[CH:16][N:17]([C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[N:18]=2)[N:8]=[CH:9][C:10]=1[C:11](OCC)=[O:12])[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([NH:4][C:5]1[C:6]2[C:7](=[CH:16][N:17]([C:19]([O:22][CH3:23])([CH3:20])[CH3:21])[N:18]=2)[N:8]=[CH:9][C:10]=1[CH2:11][OH:12])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20038761HCID 20038761, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20038774HCID 20038774, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 7-allylamino-2-(2-methoxy-2-propyl)-2H-pyrazolo[4,3-b]pyridine-6-carboxylate (2.38 g, 7.5 mmol) in dry THF (tetrahydrofuran) (25 ml) was added dropwise to an ice-cooled suspension of lithium aluminium hydride (285 mg, 7.5 mmol) in dry THF (15 ml). The mixture was stirred at room temperature, under nitrogen, for 24 h, then water (0.3 ml), 10% sodium hydroxide solution (0.3 ml) and water (0.85 ml) were added sequentially. The mixture was filtered through Kieselguhr, the solvent was evaporated in vacuo, and the residual solid was recrystallised from ethyl acetate to give the title compound as needles (1.87 g, 90%), m.p. 152°-154° C. Found: C, 60.58; H, 7.21; N, 20.26C14H20N4O2 requires C, 60.84; H, 7.29; N, 20.27%

Workup

  1. temperaturecooled
  2. filtrationThe mixture was filtered through Kieselguhr
  3. customthe solvent was evaporated in vacuo
  4. customthe residual solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-4f5f5097626844d186df5bbee9b3a1fc
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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