1,4-Dioxane--water (1/1) → HCID 57928026, compound

HRID 657109Notes

Reaction equation

HRID 657109 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:4]=2[N:5]=[C:6](/[CH:8]=C/C2C=CC=CC=2)[N:7]=1.[O:21]1CCOCC1.O>O=[Os](=O)(=O)=O>[Cl:1][C:2]1[C:3]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:4]=2[N:5]=[C:6]([CH:8]=[O:21])[N:7]=1

Participants

4

Reactant 2

HCID 218864351,4-Dioxane--water (1/1)HCID 57928091HCID 57928091, compound

Product 1

HCID 57928026HCID 57928026, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Conditions

Temperature
0 °C

Procedure

4-Chloro-2-[(E)-2-phenylethenyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (0.18 g, 0.64 mmol) was dissolved in a 2:1 solution of 1,4-dioxane/water (6 mL) and cooled to 0° C. NaIO4 (0.314 g, 1.47 mmol) and catalytic OsO4 (1 mL, 4% aq. solution) were added and the solution was then stirred at ambient temperature overnight. The reaction solution was concentrated under vacuum, diluted with water, and extracted with 10% MeOH/DCM (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/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired compound (0.05 g, 44%).

Workup

  1. concentrationThe reaction solution was concentrated under vacuum
  2. additiondiluted with water
  3. extractionextracted with 10% MeOH/DCM (4×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was then purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-ca49ec5546f54321973c594a6df5a913
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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