Reacción #1973969

Ecuación de reacción

product

N-(6-bromonaphthalen-2-yl)methanesulfonamide

sodium carbonate

1-(3,5-diiodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

→

title compound

Rendimiento 11.0%

N-(6-(5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-iodo-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide

Rendimiento 11.0%

Disolventes

toluene

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otromicrowaved at 100° C. for 30 min
2. 2
   TemperaturaThe mixture was cooled
3. 3
   Otropartitioned with ethyl acetate and 1M HCl
4. 4
   LavadoThe organic layer was washed with saturated sodium bicarbonate, brine
5. 5
   Secadodried with sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroThe residue was chromatographed on silica eluting with ethyl acetate/hexane (2:3 to 4:1)

Procedimiento

A mixture of the product from Part B 1-(3,5-diiodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (118 mg, 0.25 mmol), the product from Example 2A, Part B (87 mg, 0.25 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride CH2Cl2 complex (10.21 mg, 0.013 mmol) and sodium carbonate (0.250 ml, 0.25 mmol) in toluene (1.0 ml) and ethanol (1.0 ml) was sparged with nitrogen for 5 min and microwaved at 100° C. for 30 min. The mixture was cooled and partitioned with ethyl acetate and 1M HCl. The organic layer was washed with saturated sodium bicarbonate, brine, dried with sodium sulfate, filtered and evaporated. The residue was chromatographed on silica eluting with ethyl acetate/hexane (2:3 to 4:1) to give the title compound (16 mg, 11%). 1H NMR (300 MHz, DMSO-D6) δ ppm 3.08 (s, 3 H) 3.35 (s, 3 H) 5.67 (d, J=8.09 Hz, 1 H) 7.42 (dd, J=8.82, 2.21 Hz, 1 H) 7.59 (d, J=2.57 Hz, 1 H) 7.73 (m, 2 H) 7.81 (d, J=8.09 Hz, 1 H) 7.95 (m, 3 H) 8.09 (s, 1 H) 10.06 (s, 1 H) 11.47 (s, 1 H). MS (ESI−) m/z 562 (M−H)+.

Fuente