Chloroform → HCID 53831111, compound

HRID 1416484Notes

Reaction equation

HRID 1416484 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:32])[CH2:30][OH: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.C(Cl)(Cl)Cl>CO.[Pd]>[OH:32][CH:29]([CH2:30][OH: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

5

Reactant 2

HCID 6212ChloroformHCID 67581915HCID 67581915, compound

Product 1

HCID 53831111HCID 53831111, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(RS)-(2,3-dihydroxypropyl)oxy]quinazoline (930 mg) in methanol (10 ml) is added 10% palladium/carbon (280 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 15 hours. To the reaction mixture is added chloroform (30 ml), and the mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in methanol-chloroform, and the solution is filtered, and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in acetone, and the solution is allowed to stand at room temperature, and the precipitated crystals are separated by filtration to give 4-[(RS)-(2,3-dihydroxypropyl)oxy]-2-(1-piperazinyl)quinazoline (355 mg) as crystals.

Workup

  1. filtrationthe mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. dissolutionThe residue is dissolved in methanol-chloroform
  4. filtrationthe solution is filtered
  5. customthe filtrate is evaporated to dryness under reduced pressure
  6. dissolutionThe residue is dissolved in acetone
  7. customto stand at room temperature
  8. customthe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-49d9e9b1937d4f13a3d1dd4975b5180f
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

Loading…