HCID 67582123, compound → HCID 54235254, compound

HRID 1416506Notes

Reaction equation

HRID 1416506 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][CH2:28][C@@H:29]([OH:34])[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:34][C@@H:29]([C@H:30]([OH:33])[CH2:31][OH:32])[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[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[N:26]=1

Participants

4

Reactant 1

HCID 67582123HCID 67582123, compound

Product 1

HCID 54235254HCID 54235254, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(Benzyloxycarbonyl)piperazin-1-yl]-4-[(2R,3R)-(2,3,4-trihydroxybutan-1-yl)oxy]quinazoline (1.5 g) is dissolved in methanol (40 ml), and thereto is added 1% palladium/carbon (0.15 g), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 20 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure to give4-[(2R,3R)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (1.0 g). A part of this 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 to give4-[(2R,3R)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (1.0 g)
  3. customA part of this product is recrystallized from ethanol
  4. customto give a product

Sources & evidence

ORD record
ord-cb7e903128d543309ddb9ca6ba97210f
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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