Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Azetidine | HCID 10422 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 178505981 | HCID 178505981 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | HCID 178505982 | HCID 178505982 | 59.4% |
Reaction Steps
A mixture containing N-(6-chloro-2-cyclohexylpyrimidin-4-yl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine (78 mg, 0.22 mmol), N, N-diisopropylethylamine (158 μL, 0.91 mmol), azetidine (45 μL, 0.67 mmol) and n-butanol (6 mL) was heated at 125° C. for 20 min in the microwave. The reaction mixture was cooled to room temperature and the resulting solid was filtered and the solid washed with Et2O, sNH4Cl and Et2O. The resulting solid was air dried to give the title compound as a white solid (48 mg, 58%). MS (ES+) m/e=368. 1H NMR: (DMSO) 1.08-1.92 (10H, m), 2.26-2.58 (3H, m), 3.89-4.06 (4H, m), 6.50 (1H, brs), 8.32-8.62 (2H, m), 9.79 (1H, s), 13.03 (1H, s)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08426425B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-44aed7528ce842adba75d9b623a310d6 |
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| Source note | uspto-grants-2013_04 |
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