10-(Benzyloxy)-2-(4-fluorobenzyl)-4,8-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo-[2,3-d]pyridazine-1,9(2H,6H)-dione → 2-(4-Fluorobenzyl)-10-hydroxy-4,8-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494095Notes

Reaction equation

HRID 494095 reaction equation
C([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:14]=[C:13]([CH3:27])[C:12]=2[N:11]2[CH2:28][CH2:29][N:30]([CH3:33])[C:31](=[O:32])[C:10]=12)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C.C(#N)C>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:15]2[C:16](=[O:18])[C:17]3[C:9]([OH:8])=[C:10]4[C:31](=[O:32])[N:30]([CH3:33])[CH2:29][CH2:28][N:11]4[C:12]=3[C:13]([CH3:27])=[N:14]2)=[CH:21][CH:22]=1

Participants

5

Reactant 1

HCID 6886362910-(Benzyloxy)-2-(4-fluorobenzyl)-4,8-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo-[2,3-d]pyridazine-1,9(2H,6H)-dione

Product 1

HCID 547069002-(4-Fluorobenzyl)-10-hydroxy-4,8-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 10-(benzyloxy)-2-(4-fluorobenzyl)-4,8-dimethyl-7,8-dihydropyrazino-[1′,2′:1,5]pyrrolo-[2,3-d]pyridazine-1,9(2H,6H)-dione (17 mg, 38 μmol) and Pearlman's catalyst (6.0 mg, 20% Pd(OH)2 on carbon) in ethanol (20 mL) was stirred under an atmosphere of hydrogen gas (1 atm) at room temperature for 30 minutes. The reaction mixture was diluted with acetonitrile and filtered through a pad of Celite. The filtrate was concentrated under vacuum, and the residue triturated with a mixture of methanol and diethyl ether. A solid precipitate was obtained by filtration to provide the titled compound.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue triturated with a mixture of methanol and diethyl ether
  4. customA solid precipitate was obtained by filtration

Sources & evidence

ORD record
ord-c1c698ccd4174a86af731850c3515450
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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