Water → HCID 86676920, compound

HRID 2200787Notes

Reaction equation

HRID 2200787 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[C:16](/[CH:18]=C/OCC)[N:15]=[C:14]([C:23]([F:26])([F:25])[F:24])[N:13]=3)[CH2:7][CH2:6]2)O[CH2:3][CH2:2]1.[OH2:27].I([O-])(=O)(=O)=[O:29].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[O:27]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[N:13]=[C:14]([C:23]([F:26])([F:25])[F:24])[N:15]=[C:16]([CH:18]=[O:29])[CH:17]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 962Water2×HCID 23667635Sodium periodateHCID 71257637HCID 71257637, compound

Product 1

HCID 86676920HCID 86676920, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

4-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-6-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyrimidine (2.50 g, 6.68 mmol) was dissolved in 1,4-dioxane (190 mL,) and water (48 mL) and then sodium periodate (4.3 g, 20. mmol, Aldrich) was added, followed by a 4% solution of osmium tetraoxide in water (1.47 mL, 0.232 mmol). The solution began to form a whitish solid after a few minutes. The reaction was stirred at 25° C. for 48 hours until LCMS analysis of the reaction mixture showed no starting material present. The reaction was transferred to a separatory funnel and partitioned between water and EtOAc, the phases were separated, and then the aqueous phase was washed with EtOAc. The combined organic phase was washed with water, then saturated NaCl, dried over MgSO4 and filtered and stripped to dryness to leave the crude product. The crude material was used in the next reaction without purification. 1H NMR (400 MHz, CDCl3) δ: 10.01 (s, 1H), 7.33 (s, 1H), 5.38 (m, 1H), 3.97 (s, 4H), 1.20-2.05 (m, 8H).

Workup

  1. customto form a whitish solid after a few minutes
  2. customThe reaction was transferred to a separatory funnel
  3. custompartitioned between water and EtOAc
  4. customthe phases were separated
  5. washthe aqueous phase was washed with EtOAc
  6. washThe combined organic phase was washed with water
  7. dry with materialsaturated NaCl, dried over MgSO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1d75cfbf40024684a253e829bd4449aa
Source dataset
uspto-grants-2016_06
Patent number
US09359358B2

Reaction notes

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