Methanol → HCID 57098847, compound

HRID 1416471Notes

Reaction equation

HRID 1416471 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)[C@H:30]([OH:34])[C@@H:29]3[OH:35])[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.[CH3:36][OH:37]>[Pd]>[OH:35][C@H:29]1[C@@H:30]([OH:34])[C@H:31]([O:37][CH3:36])[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[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[N:26]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 67582894HCID 67582894, compound

Product 1

HCID 57098847HCID 57098847, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1S,2S,3S,4R)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]quinazoline [cf. Example 33(4)] (1.00 g) in methanol (15 ml) is added 10% palladium/carbon (200 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 3 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure, and the residue is dissolved in ethanol (35 ml) and thereto is added fumaric acid (242 mg). The precipitated crystals are dissolved by adding water to the mixture. The mixture is filtered and the filtrate is evaporated to dryness under reduced pressure, and the resulting residue is recrystallized from water-ethanol to give 4-[(1S,2S,3S,4R)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline 1/2 fumarate (390 mg) as crystals.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. dissolutionthe residue is dissolved in ethanol (35 ml)
  4. additionis added fumaric acid (242 mg)
  5. dissolutionThe precipitated crystals are dissolved
  6. additionby adding water to the mixture
  7. filtrationThe mixture is filtered
  8. customthe filtrate is evaporated to dryness under reduced pressure
  9. customthe resulting residue is recrystallized from water-ethanol

Sources & evidence

ORD record
ord-5091d335ff3d4b6096478cad06643076
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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