2,6-Lutidine → HCID 86667469, compound

HRID 2401772Notes

Reaction equation

HRID 2401772 reaction equation
[CH3:1][Si:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH:23]=C)=[N:8]1.[O:27]1CCOCC1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[N:20]1[CH:21]=[CH:22][C:17]([C:15]2[S:16][C:12]([C:9]3[N:10]=[CH:11][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:26])([CH3:25])[CH3:1])[N:8]=3)=[C:13]([CH:23]=[O:27])[N:14]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 79372,6-LutidineHCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 68006677HCID 68006677, compound

Product 1

HCID 86667469HCID 86667469, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-4-vinyl-1,3-thiazol-2-yl]pyridine (1.43 g, 2.60 mmol) in a 3:1 mixture of 1,4-dioxane (17.5 mL, 224.6 mmol) and water (5.8 mL, 324.25 mmol) was added 2,6-lutidine (1.50 mL, 12.98 mmol) and the mixture was cooled to 0° C. Sodium metaperiodate (2.80 g, 12.98 mmol) was added followed by the addition of 4% osmium tetroxide in water (0.50 mL, 0.080 mmol) and the reaction mixture was slowly warmed to ambient temperature and allowed to stir overnight. Water (10 mL) was added. The resulting yellow precipitate was collected by filtration, washed with water, ether and MeOH. The filtrate was concentrated under reduced pressure and dried on the high vac to give the title compound (1.0 g, yield 99%). LCMS: (FA) ES+ , 388. 1H NMR (400 MHz, d6-DMSO) δ: 10.70 (s, 1H), 6:9.05 (s, 1H), 8.79-8.80 (dd, J=1.5 Hz, 2H), 7.98-8.0 (dd, J=1.5 Hz, J=1.7 Hz, 2H), 5.64-5.66 (s, br, 2H), 3.64-3.68 (m, 2H), 0.870-0.90 (m, 2H), −0.03 (s, 9H).

Workup

  1. temperaturethe reaction mixture was slowly warmed to ambient temperature
  2. filtrationThe resulting yellow precipitate was collected by filtration
  3. washwashed with water, ether and MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customdried on the high vac

Sources & evidence

ORD record
ord-41fdfd23c8da4703b2ee76af0188e424
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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