Chloroform → HCID 90402322, compound

HRID 576708

Reaction equation

HRID 576708 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[N:4][N:3]=1.C(Cl)(Cl)Cl.CC#N.I([O-])(=O)(=O)=[O:26].[Na+]>O.O.[Ru](=O)=O>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:10](=[O:26])[C:5]2=[N:4][N:3]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6342AcetonitrileHCID 17998723tert-Butyl 3-bromo-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylateHCID 23667635Sodium periodate

Product 1

HCID 90402322HCID 90402322, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 16211523Ruthenium dioxide hydrateCatalyst3×HCID 962WaterSolvent2×

Procedure

To a vigorously stirred solution of tert-butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (1.0 g, 3.3 mmol) in 1:1 CHCl3:MeCN (25 mL) was added ruthenium (IV) oxide hydrate (65 mg, 0.43 mmol) and sodium metaperiodate (3.3 g, 15.5 mmol) in water (31 mL). After 1 h, additional ruthenium (IV) oxide hydrate (50 mg) was added. After another hour, a final portion of ruthenium (IV) oxide hydrate (30 mg) was added. Stirring was maintained for 30 minutes and then water was added. The entire mixture was extracted with CHCl3. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford a green oil. Purification by chromatography (SiO2; hexanes—100% EtOAc) provided the desired product as a white solid (663 mg, 63%). MS (ESI): mass calcd. for C10H13BrN4O3, 316.0; m/z found, 317.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 4.41-4.28 (m, 2H), 4.26-4.22 (m, 2H), 1.58 (s, 9H).

Workup

  1. waitAfter another hour
  2. temperaturewas maintained for 30 minutes
  3. extractionThe entire mixture was extracted with CHCl3
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a green oil
  8. customPurification by chromatography (SiO2; hexanes—100% EtOAc)

Sources & evidence

ORD record
ord-0f2b763345344f99945c83526da9f430
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Linked notes

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