Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tert-Butylamine | HCID 6385 | — |
| Reactant | HCID 89793970 | HCID 89793970 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 89793968 | HCID 89793968 | 81% |
Reaction Steps
A solution of 8-bromo-2-chloro-3-cyclobutylquinazolin-4(3H)-one (294.7 mg, 0.94 mmol), tert-butylamine (Aldrich; 1.5 mL, 14.27 mmol), and NMP (0.5 mL) was heated in a sealed microwave vial at 120° C. for 30 min. The reaction mixture was then partitioned between EtOAc (60 mL) and water (40 mL). The organic layer was separated and sequentially washed water (40 mL) and brine (40 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-(tert-butylamino)-3-cyclobutylquinazolin-4(3H)-one (266 mg, 0.759 mmol, 81% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.87 (1H, dd, J=7.6, 1.2 Hz), 7.84 (1H, dd, J=7.8, 1.4 Hz), 6.98 (1H, t, J=7.8 Hz), 5.88 (1H, s), 4.47-4.60 (1H, m), 2.54-2.64 (2H, m), 2.06-2.20 (2H, m), 1.56-1.66 (2H, m), 1.52 (9H, s). m/z (ESI, +ve) 349.9/352.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09394297B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-a7f4a298086e4772bf460a08c8dc6108 |
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| Source note | uspto-grants-2016_07 |
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