Lithium Hydroxide → Pyrazolo[3,4-d]pyrimidin-4-one

HRID 411585Notes

Reaction equation

HRID 411585 reaction equation
ClC1C=CC=C(Cl)C=1[N:9]1[C:13]2=[N:14][C:15](CC3C=CC(CC(OCC)=O)=CC=3)=[N:16][C:17](=[O:18])[C:12]2=[C:11](C(C)C)[NH:10]1.C1COCC1.[OH-].[Li+]>O>[N:9]1[C:13]2=[N:14][CH:15]=[N:16][C:17](=[O:18])[C:12]2=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178470661HCID 178470661, compound

Product 1

HCID 22252149Pyrazolo[3,4-d]pyrimidin-4-oneYield 313.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ester, 1-(2,6-dichlorophenyl)-3-isopropyl-6-(4-(carbethoxymethyl)benzyl)pyrazolo[3,4-d]pyrimidin-4-one (1.20 g, 2.4 mmol) was stirred at RT overnight with THF (50 mL), water (15 mL) and 1 N lithium hydroxide (7.20 mL). The solution was evaporated to near dryness, diluted with 1 N hydrochloric acid, vigorously stirred and the solid was collected by filtration and dried under high vacuum to give 1-(2,6-dichlorophenyl)-3-isopropyl-6-(4-carboxymethyl)benzyl)pyrazolo[3,4-d]pyrimidin-4-one (1.01 g, 89% yield) as a white solid, mp 212-214° C. Mass Spec.: 471 (M+H)+.

Workup

  1. customThe solution was evaporated
  2. additiondiluted with 1 N hydrochloric acid
  3. filtrationthe solid was collected by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-0fd34822cbd440a0853b57b2b3e44d0e
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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