Triacetoxyperiodinane → Triacetoxyperiodinane

HRID 341496Notes

Reaction equation

HRID 341496 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]3)[O:18][N:17]=2)[N:3]=1.[CH3:28][C:29]([O:31][I:32]1([O:46][C:47]([CH3:49])=[O:48])([O:42][C:43]([CH3:45])=[O:44])[O:41][C:39](=[O:40])[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]1=2)=[O:30]>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([N:21]3[CH2:22][CH2:23][C:24](=[O:27])[CH2:25][CH2:26]3)[O:18][N:17]=2)[N:3]=1.[CH3:45][C:43]([O:42][I:32]1([O:46][C:47]([CH3:49])=[O:48])([O:31][C:29]([CH3:28])=[O:30])[O:41][C:39](=[O:40])[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]1=2)=[O:44]

Participants

5

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 668032151-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)piperidin-4-ol2×

Product 2

HCID 159087TriacetoxyperiodinaneHCID 668031631-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)piperidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)piperidin-4-ol (Intermediate 132, 120 mg, 0.325 mmol) in DCM (20 mL) at 0 C was added Dess-Martin Periodinane (138 mg, 0.325 mmol). The resulting reaction mixture was stirred at room temperature for 2 h and then further Dess-Martin Periodinane (138 mg, 0.325 mmol) was added. The reaction mixture was stirred for a further 16 h at room temperature and then quenched with a saturated sodium bicarbonate aq. solution (10 mL). The resulting bi-layer was separated and the organics washed further with a 1M aq. HCl solution (10 mL). Organics were dried over magnesium sulfate, evaporated to dryness and purified by silica chromatography (0 to 3% MeOH in DCM) to afford the title compound as an off-white solid (Dess-Martin Periodinane impurities (17%) also present) (179 mg, 150%). Method C HPLC-MS: MH+ requires m/z=367. Found: m/z=367, Rt=1.14 min (74%).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was stirred for a further 16 h at room temperature
  3. customquenched with a saturated sodium bicarbonate aq. solution (10 mL)
  4. customThe resulting bi-layer was separated
  5. washthe organics washed further with a 1M aq. HCl solution (10 mL)
  6. dry with materialOrganics were dried over magnesium sulfate
  7. customevaporated to dryness
  8. custompurified by silica chromatography (0 to 3% MeOH in DCM)

Sources & evidence

ORD record
ord-55f9095277094c118b1d19a9d6003cc5
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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