Acetone → 3-(5,6-Dihydroxyhexyl)-1-methylthymine

HRID 361520Notes

Reaction equation

HRID 361520 reaction equation
[CH2:1]([N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16])[CH2:2][CH2:3]CC=C.C[N+]1([O-])CC[O:21]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:33][C:34]([CH3:36])=[O:35]>C(O)(C)(C)C.O.[Os](=O)(=O)(=O)=O>[OH:35][CH:34]([CH2:36][OH:21])[CH2:33][CH2:3][CH2:2][CH2:1][N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16]

Participants

8

Reactant 4

HCID 180AcetoneHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 232959493-(5-Hexenyl)-1-methylthymine

Product 1

HCID 232879373-(5,6-Dihydroxyhexyl)-1-methylthymineYield 89%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 3-(5-hexenyl)-1-methylthymine (2.00 g, 9 mmol), 4-methylmorpholine-N oxide (1.17 mg, 10 mmol), and a 2.5% sol. in t-butanol of osmium tetroxide (0.15 mL ) in acetone (15 mL) and water (10 mL) was stirred for 20 hours. After addition of a saturated solution of sodium hydrosulfite (10 mL) and 15 minutes of stirring, the reaction mixture was extracted with 20% ethanolldichloromethane (4×40 mL). The combined organic layers were dried over sodium sulfate and the solvent evaporated under vacuum to a give white solid residue. The solid was recrystallized in ethanol to yield 2.00 g (89%) of 3-(5,6-dihydroxyhexyl)-1-methylthymine (inventive compound no. 1907).

Workup

  1. extractionthe reaction mixture was extracted with 20% ethanolldichloromethane (4×40 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customthe solvent evaporated under vacuum to a give white solid residue
  4. customThe solid was recrystallized in ethanol

Sources & evidence

ORD record
ord-a55cb05f6275408cbf20e40ce11b2ece
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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