Chloroform → HCID 90402531, compound

HRID 576691

Reaction equation

HRID 576691 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][N:14]([C:16]([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[O:17])[CH2:15][C:10]2=[N:9][N:8]=1.C(Cl)(Cl)Cl.CC#N.I([O-])(=O)(=O)=[O:33].[Na+]>O.O.[Ru](=O)=O>[O:33]=[C:15]1[N:14]([C:16]([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[O:17])[CH2:13][CH2:12][N:11]2[C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[N:8][N:9]=[C:10]12

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 904024312-(trimethylsilyl)ethyl 3-(pyrazin-2-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Product 1

HCID 90402531HCID 90402531, compoundYield 367.9%

Reagents, catalysts & solvents 2

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 962WaterSolvent2×

Procedure

To a vigorously stirred solution of 2-(trimethylsilyl)ethyl 3-(pyrazin-2-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (172 mg, 0.5 mmol) in 1:1 CHCl3:MeCN (3.8 mL) was added a solution of ruthenium (IV) oxide hydrate (9.8 mg, 0.07 mmol) and sodium metaperiodate (504 mg, 2.3 mmol) in water (4.7 mL). After 4 h, the reaction mixture was diluted with water and extracted with CHCl3 (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford a green oil. Purification by chromatography (SiO2; EtOAc—10% IPA/EtOAc) provided the desired product as a white solid (663 mg, 63%). MS (ESI): mass calcd. for C15H20H6O3Si, 360.1; m/z found, 361.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 9.59 (d, J=1.5 Hz, 1H), 8.63 (d, J=2.5 Hz, 1H), 8.55 (dd, J=2.5, 1.6 Hz, 1H), 4.88-4.75 (m, 2H), 4.47-4.33 (m, 2H), 4.33-4.24 (m, 2H), 1.18-1.04 (m, 2H), 0.04-(−0.02) (m, 9H).

Workup

  1. extractionextracted with CHCl3 (×3)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a green oil
  6. customPurification by chromatography (SiO2; EtOAc—10% IPA/EtOAc)

Sources & evidence

ORD record
ord-ac55a7b9ab7e44c8a03ea02a561f826c
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Linked notes

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