Tetrahydrofuran → HCID 21714046, compound

HRID 650249Notes

Reaction equation

HRID 650249 reaction equation
C[N+]1([O-])CC[O:5]CC1.[C:9]([NH:12][C:13]1[C:18](=[O:19])[N:17](CC=C)[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:15][CH:14]=1)(=[O:11])[CH3:10].S([O-])([O-])(=O)=S.[Na+].[Na+].[O:36]1[CH2:40][CH2:39][CH2:38]C1>[Os](=O)(=O)(=O)=O>[C:9]([NH:12][C:13]1[C:18](=[O:19])[N:17]([CH2:38][CH:39]([OH:5])[CH2:40][OH:36])[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:15][CH:14]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 21714057HCID 21714057, compound

Product 1

HCID 21714046HCID 21714046, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

50% aqueous N-methylmorpholine-N-oxide (1.55 ml, 6.6 mmol) and 0.157 N aqueous osmium tetroxide (1.06 ml, 0.165 mmol) were added to a solution of 5-acetylamino-1-allyl-6-oxo-2-phenyl-1,6-dihydropyrimidine (888.6 mg, 3.3 mmol) in tetrahydrofuran (13 ml), and the mixture was stirred at room temperature for 2 days. After saturated aqueous sodium thiosulfate was added, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated saline. After dried over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1) whereby the title compound (1.06 g, quant) was obtained as white solid. 1H-NMR (CDCl3); 2.25 (3H, s), 2.40-2.58 (1H, m), 3.29-3.63 (3H, complex), 3.78-3.95 (1H, m), 4.08-4.26 (2H, m), 7.41-7.54 (5H, s), 8.04 (1H, m), 9.00 (1H, s); MS (FAB) m/z=304 (M+1)

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated saline
  3. dry with materialAfter dried over anhydrous sodium sulfate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1) whereby the title compound (1.06 g, quant)
  6. customwas obtained as white solid

Sources & evidence

ORD record
ord-b07a26fe8fb94c72a6de357795effea5
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

Loading…