HCID 54757412, compound → HCID 54757413, compound

HRID 1782168Notes

Reaction equation

HRID 1782168 reaction equation
[N:1]([CH:4]([C:8]1[N:9]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10](=[O:18])[C:11]2[C:16]([CH3:17])=[N:15][S:14][C:12]=2[N:13]=1)[CH:5]([CH3:7])[CH3:6])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH:4]([C:8]1[N:9]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:10](=[O:18])[C:11]2[C:16]([CH3:17])=[N:15][S:14][C:12]=2[N:13]=1)[CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 1

HCID 54757412HCID 54757412, compound

Product 1

HCID 54757413HCID 54757413, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(1-azido-2-methyl-propyl)-5-benzyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 29) (6.8 g, 19.2 mmol) in methanol (400 ml) was added 5% Pd/C (1 g, 20% by wt.) and the resulting mixture was stirred at r.t. in an atmosphere of H2 and the progress of the reaction was monitored by MS. After the disappearance of the starting material the reaction mixture was filtered through celite and washed with EtOAc. Concentration of the filtrate provided 6-(1-amino-2-methyl-propyl)-5-benzyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (5.42 g, 86%).

Workup

  1. filtrationAfter the disappearance of the starting material the reaction mixture was filtered through celite
  2. washwashed with EtOAc

Sources & evidence

ORD record
ord-148c9e5d6a564c5abd1dfa5e526de3ab
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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