Nitrogen → 3-(9-fluoro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazin-7-yl)-2,6-dimethylpyrimidin-4(3H)-one

To a solution of 9-fluoro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazin-7-amine (2.00 g, 9.61 mmol) in anhydrous CH2Cl2 (50 mL) was added trimethylaluminum (48 mL, 48 mmol, 1 M in heptane) slowly under N2. Upon the end of addition the mixture was stirred at rt for 40 min, followed by addition of a solution of methyl 3-acetaminocrotonate (2.66 g, 16.92 mmol) in anhydrous CH2Cl2 (30 mL) dropwise. The reaction mixture was stirred at rt for another 5 h, then quenched with an appropriate amount of water. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a white solid (1.00 g, 33.0%). The compound was characterized by the following spectroscopic data:

1. additionUpon the end of addition the mixture
2. stirringThe reaction mixture was stirred at rt for another 5 h
3. customquenched with an appropriate amount of water
4. washThe organic phase was washed with brine
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated in vacuo

ORD-Eintrag

ord-b72072a9cb5e4685a4d2a23a95e1ea74

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09434695B2