Reacción #218739

Ecuación de reacción

product

6-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-5-[4-(S)-hydroxy-2-isoxazolidinylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

N-bromosuccinimide

sodium bicarbonate

2-methylindole

→

sub-title compound

Methyl 1,2,3,4-tetrahydro-3-methyl-6-[(2-methyl-1H-indol-3-yl)methyl]-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe phases were separated
2. 2
   Extracciónthe aqueous phase extracted with dichloromethane (100 ml)
3. 3
   SecadoThe combined organic extracts were dried over anhydrous magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated under reduced pressure
6. 6
   OtroThe residue was purified by column chromatography over silica
7. 7
   Lavadoeluting with ethyl acetate/i-hexane (1:3)

Procedimiento

A solution of the product of example 3, part a), (7 g) and N-bromosuccinimide (4.42 g) in chloroform (140 ml) was refluxed under illumination from a tungsten lamp for 2 h. The solution was cooled to room temperature, saturated aqueous sodium bicarbonate solution (140 ml) and 2-methylindole (5.92 g) were added and the mixture stirred rapidly for 48 h. The phases were separated and the aqueous phase extracted with dichloromethane (100 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ethyl acetate/i-hexane (1:3) to give the sub-title compound as a pale brown solid (6.68 g). MS(ESI) 440 [M+H]+. δ 1HCDCl3 0.87 (6H, d), 2.11-2.21 (1H, m), 2.42 (3H, s), 3.38 (3H, s), 3.61 (2H, d), 3.99 (3H, s), 4.22 (2H, s), 7.08 (1H, t), 7.15 (1H, t), 7.31 (1H, d), 7.46 (1H, d), 7.91 (1H, s, br).

Fuente