Potassium Phosphate, Tribasic → 5-[4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]pyrimidine-2-carboxylic acid

Temperatur

120 °C

To a solution of Example 292 (100 mg, 0.227 mmol) in THF (3 mL) and water (1 mL) was added tetra-n-butylammonium bromide (146 mg, 0.454 mmol), potassium phosphate (144 mg, 0.681 mmol), 5-bromopyrimidine-2-carboxylic acid (70 mg, 0.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol). The reaction was heated at 120° C. under microwave irradiation for 30 minutes then cooled to r.t. The mixture was partitioned between DCM (50 mL) and water (50 mL). The aqueous phase was acidified with 1M HCl and the resulting precipitate was collected, washed with water (2×10 mL), Et2O (3×10 mL) and dried in vacuo to yield the title compound (16 mg, 16%) as an off-white solid. δH (CD3OD) 9.06 (2H, br s), 8.57 (1H, br. s), 7.32 (1H, s), 7.31 (1H, d, J 8.5 Hz), 7.07 (1H, d, J 8.5 Hz), 4.41-4.34 (2H, m), 4.07-4.01 (2H, m), 2.83 (2H, s), 1.34 (6H, s). LCMS (ES+) 875.0 (2M+H)+, RT 2.43 minutes (Method 1).

1. temperaturethen cooled to r.t
2. customThe mixture was partitioned between DCM (50 mL) and water (50 mL)
3. customthe resulting precipitate was collected
4. washwashed with water (2×10 mL), Et2O (3×10 mL)
5. customdried in vacuo

ORD-Eintrag

ord-4ce93b9c3176440b82c144bad5487dd5

Quelldatensatz

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08242116B2