Water → HCID 20038781, compound

HRID 1904273Notes

Reaction equation

HRID 1904273 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[C:7](=[CH:16][N:17]([CH3:19])[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+]>C1COCC1>[CH2:1]([NH:4][C:5]1[C:6]2[C:7](=[CH:16][N:17]([CH3:19])[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 20038779HCID 20038779, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20038781HCID 20038781, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 7-allylamino-2-methyl-2H-pyrazolo-[4,3-b]pyridine-6-carboxylate (100 mg, 0.38 mmol) in dry THF (2 ml) was added dropwise to an ice-cooled suspension of lithium aluminium hydride (15 mg, 0.39 mmol) in THF (1 ml). The mixture was stirred at room temperature, under nitrogen, for 16 h, then water (0.03 ml), 10% sodium hydroxide solution (0.4 ml) and water (0.09 ml) were added sequentially. The solids were filtered off and washed with ethyl acetate. The solution was evaporated in vacuo to give a solid, which was recrystallised from ethyl acetate to give the title compound as needles (40 mg, 48%), m.p. 151°-159° C.

Workup

  1. temperaturecooled
  2. filtrationThe solids were filtered off
  3. washwashed with ethyl acetate
  4. customThe solution was evaporated in vacuo
  5. customto give a solid, which
  6. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b303a245d199440f89e3c1826d37e833
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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