Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | HCID 66741956 | HCID 66741956 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86662317 | HCID 86662317 | 89.6% |
Reaction Steps
To a suspension of 6-chloro-4-(5-(1-hydroxy-2-methylpropan-2-yloxy)pyridin-2-ylamino)-2-methylpyridazin-3(2H)-one (750 mg, 2.31 mmol, Eq: 1.00) in DCM (100 ml) was added Dess-Martin periodinane (1.27 g, 3.00 mmol, Eq: 1.30). The reaction mixture was stirred at room temperature for about 40 minutes. Ether was added (100 mL) followed by 50 ml NaOH solution (1 M). The mixture was stirred for additional 15 minutes and transferred to separatory funnel. The organic layer was washed with equal volume of NaOH (1M) water (50 mL), dried (Na2SO4) and evaporated under vacuum to afford the desired product (668 mg) as a light brown powder. (M+H)=323 m/e. 1H NMR (400 MHz, DMSO-d6) 8 ppm 1.36 (s, 6 H) 3.68 (s, 3 H) 7.43-7.47 (m, 1 H) 7.51-7.55 (m, 1 H) 8.10 (dd, J=3.03, 0.51 Hz, 1 H) 8.27 (s, 1 H) 9.69 (s, 1 H) 9.82 (s, 1 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08889682B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-d8a41e7afc18404fbac3a139a96e42a2 |
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| Source note | uspto-grants-2014_11 |
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