Sodium Carbonate → 2,5-Dichloro-4-(6-methylsulfanylbenzo[b]thiophen-2-yl)-pyrimidine

To a stirred solution of 6-methylsulfanylbenzo[b]thiophene (1.41 g, 7.82 mmol) and triisopropylborate (1.80 mL, 7.82 mmol) in THF (20 mL) at −78° C. under nitrogen is added lithium diisopropylamine (4.3 mL, 2 M solution). The reaction is allowed to slowly warm to room temperature. An aqueous solution of Na2CO3 (2.50 g, 23.5 mmol, in 11 mL of water) is added, followed by the addition of 2,4,5-trichloropyrimidine (1.58 g, 8.60 mmol) and [1,1-bis(diphenylphospheno)ferrocene]palladium (II) chloride (0.32 g, 0.39 mmol). The reaction mixture is heated at 60° C. under nitrogen for 1 hour. After being cooled to room temperature, the suspension is filtered and the solid is washed with water and ethyl acetate then dried under vacuum. The crude product is purified by chromatography on silica gel, eluting with dichloromethane:hexanes 2:8 to 3:7, to give the title product as a light yellow solid (0.19 g).

1. temperatureThe reaction mixture is heated at 60° C. under nitrogen for 1 hour
2. temperatureAfter being cooled to room temperature
3. filtrationthe suspension is filtered
4. washthe solid is washed with water and ethyl acetate
5. customthen dried under vacuum
6. customThe crude product is purified by chromatography on silica gel
7. washeluting with dichloromethane:hexanes 2:8 to 3:7

ORD record

ord-4ff1c7c60ecb43359a2c99cadc8cd989

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547691B2