HCID 67583605, compound → HCID 53831110, compound

HRID 1416508Notes

Reaction equation

HRID 1416508 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: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>CO.[Pd]>[OH:32][C@H: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

4

Reactant 1

HCID 67583605HCID 67583605, compound

Product 1

HCID 53831110HCID 53831110, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(Benzyloxycarbonyl)piperazin-1-yl]-4-[(2R)-(2,3-dihydroxypropan-1-yl)oxy]quinazoline (5.8 g) is dissolved in methanol (50 ml), and thereto is added 10% palladium/carbon (0.6 g), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature overnight. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure, and the residue is recrystallized from methanol to give 4-[(2R)-(2,3-dihydroxypropan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (1.4 g).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-d5a55eb9d3e04622877e8b97acde8cb4
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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