1,4-Dioxane--water (1/1) → HCID 86635373, compound

HRID 657151Notes

Reaction equation

HRID 657151 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:19][CH2:18][CH2:17][O:16][C:4]=2[N:5]=[C:6](/[CH:8]=C/C2C=CC=CC=2)[N:7]=1.[O:20]1CCOCC1.O>O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[C:3]2[CH2:19][CH2:18][CH2:17][O:16][C:4]=2[N:5]=[C:6]([CH:8]=[O:20])[N:7]=1

Participants

5

Reactant 2

HCID 218864351,4-Dioxane--water (1/1)HCID 86635372HCID 86635372, compound

Product 1

HCID 86635373HCID 86635373, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 4-chloro-2-[(E)-2-phenylethenyl]-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine (0.21 g, 0.79 mmol) was dissolved in a 2:1 solution of 1,4-dioxane/water (6 mL) and cooled to 0° C. NaIO4 (0.50 g, 2.4 mmol) and catalytic OsO4 (0.25 mL, 4% aq. solution) were added and the solution was then stirred at ambient temperature for 2 h. The reaction solution was diluted with water (10 mL) and extracted with EtOAc (4×). The organic layers were combined, dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was then purified by column chromatography (silica gel) using a DCM-MeOH (90:10) to yield the desired compound as an off-white solid (0.055 g, 36%).

Workup

  1. extractionextracted with EtOAc (4×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude residue was then purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-205ce5e9f02c474ab93073c1f5b16f79
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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