1,4-Dioxane → HCID 57153789, compound

HRID 1416492Notes

Reaction equation

HRID 1416492 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:33])[C@@H: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.O1CCOCC1>CO.[Pd]>[OH:33][C@H:29]([C@@H: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

5

Reactant 2

HCID 312751,4-DioxaneHCID 67581931HCID 67581931, compound

Product 1

HCID 57153789HCID 57153789, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(Benzyloxycarbonyl)piperazin-1-yl]-4-[(2S,3S)-(2,3-dihydroxybutan-1-yl)oxy]quinazoline (5.1 g) is dissolved in methanol (90 ml)--dioxane (10 ml), and thereto is added 10% palladium/carbon (0.5 g), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 16 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure to give 4-[(2S,3S)-(2,3-dihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (3.3 g).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-598540da6ccb420d81c0d30870dc5074
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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