HCID 67581949, compound → HCID 57098847, compound

HRID 1416477Notes

Reaction equation

HRID 1416477 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][C@H:28]3[CH2:32][C@@H:31]([O:33][CH3:34])[C@H:30]([OH:35])[C@@H:29]3[OH:36])[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:36][C@H:29]1[C@@H:30]([OH:35])[C@H:31]([O:33][CH3:34])[CH2:32][C@@H:28]1[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 67581949HCID 67581949, compound

Product 1

HCID 57098847HCID 57098847, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1S,2S,3R,4R)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]quinazoline (600 mg) in methanol (12 ml) is added 10% palladium/carbon (120 mg), 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 give 4-[(1S,2S,3R,4R)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (415 mg) as foam.

Workup

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

Sources & evidence

ORD record
ord-4f86baab53be4a9fb8a9a1578b73537c
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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