HCID 67582830, compound → HCID 54302338, compound

HRID 1416491Notes

Reaction equation

HRID 1416491 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][CH2:28][CH:29]([OH:33])[CH:30]([OH:32])[CH3:31])[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][CH:29]([CH:30]([OH:32])[CH3:31])[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 67582830HCID 67582830, compound

Product 1

HCID 54302338HCID 54302338, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(2RS,3RS)-(2,3-dihydroxybutan-1-yl)oxy]quinazoline (950 mg) in methanol (21 ml) is added 10% palladium/carbon (109 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 8 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure, and the residue is crystallized from acetone-diethyl ether. The crystals thus obtained are recrystallized from ethanol - diethyl ether to give 4-[(2RS,3RS)-(2,3-dihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (235 mg) as crystals.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. customthe residue is crystallized from acetone-diethyl ether
  4. customThe crystals thus obtained
  5. customare recrystallized from ethanol - diethyl ether

Sources & evidence

ORD record
ord-1a412b68e070493b803f1d778569d1cc
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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