Water → 3-(5,6-Dihydroxyhexyl)-1-methyluracil

HRID 399756Notes

Reaction equation

HRID 399756 reaction equation
[CH2:1]([N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C[N+]1([O-])CC[O:20]CC1.[OH2:24].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:24][CH:5]([CH2:6][OH:20])[CH2:4][CH2:3][CH2:2][CH2:1][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15]

Participants

8

Reactant 4

HCID 962Water2×HCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 232958743-(5-Hexenyl)-1-methyluracil

Product 1

HCID 232879503-(5,6-Dihydroxyhexyl)-1-methyluracilYield 66%

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

A solution of 3-(5-hexenyl)-1-methyluracil (598 mg, 2.9 mmol), 4-methylmorpholine-N oxide (408 mg, 3,5 mmol), and a 2.5% solution of osmium tetroxide in t-butanol (3 drops) in acetone (15 ml) and water (5 ml) was stirred for 3 days. Saturated aqueous sodium hydrosulfite solution (10 ml) was added and the mixture was stirred for 15 minutes. Water (50 ml) was added and the mixture was extracted with 20% ethanol-dichloromethane (4×40 ml). The combined organic layers were dried over sodium sulfate and the solvents were evaporated under vacuum to give 3-(5,6-dihydroxyhexyl)-1-methyluracil (461 mg, 66% yield) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with 20% ethanol-dichloromethane (4×40 ml)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customthe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-d22c8b6d6b9a4117b69e0ca9496f8dd6
Source dataset
uspto-grants-1998_10
Patent number
US05824677

Reaction notes

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