HCID 67581923, compound → HCID 53859577, compound

HRID 1416500Notes

Reaction equation

HRID 1416500 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 67581923HCID 67581923, compound

Product 1

HCID 53859577HCID 53859577, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(3R)-(3,4-dihydroxybutan-1-yl)oxy]quinazoline (4.23 g) in methanol (40 ml) is added 10% palladium/carbon (634 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 18.5 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-[(3R)-(3,4-dihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (2.13 g) as crystals. A part of the product is recrystallized from ethanol to give a product having the following physical properties.

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-0d5e951f4db744a98ec2d22655868367
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

Loading…