HCID 67582099, compound → HCID 57109376, compound

HRID 1416497Notes

Reaction equation

HRID 1416497 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][CH2:28][CH2:29][C@H:30]([OH:33])[CH2:31][OH:32])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[OH:33][C@H:30]([CH2:31][OH:32])[CH2:29][CH2:28][O:27][C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([N:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)[N:26]=1

Participants

4

Reactant 1

HCID 67582099HCID 67582099, compound

Product 1

HCID 57109376HCID 57109376, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(3S)-(3,4-dihydroxybutan-1-yl)oxy]quinazoline (2.00 g) in methanol (40 ml) is added 10% palladium/carbon (300 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 21.5 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure, and the residue is washed with acetone to give 4-[(3S)-(3,4-dihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (1.10 g) as crystals.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. washthe residue is washed with acetone

Sources & evidence

ORD record
ord-3cbe79a74ee9401ca4a10bce70aa13cc
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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