تفاعل #73115

معادلة التفاعل

(R)-2-(4-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

4-(tributylstannyl)thiazole

→

title compound

المردود 18.7%

(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(4-(thiazol-4-yl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

المردود 18.7%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىcap vial
2. 2
   أخرىa stream of nitrogen was bubbled through the mixture for 2 minutes
3. 3
   أخرىThe vial was sealed
4. 4
   workup.ADDITIONThe reaction mixture was diluted with brine
5. 5
   استخلاصextracted with EtOAc
6. 6
   تجفيفdried with Na2SO4
7. 7
   أخرىthen purified by flash chromatography with a silica gel column
8. 8
   غسيلby eluting with a mixture of Hexane
9. 9
   أخرىEtOAc and then further purified by preparative HPLC

الإجراء التجريبي

(R)-2-(4-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 43, 0.11 g, 0.271 mmol), 4-(tributylstannyl)thiazole (0.10 g, 0.271 mmol, see Example 355) and Pd(PPh3)4 (31 mg, 0.0271) were dissolved in DMF in a screw cap vial and a stream of nitrogen was bubbled through the mixture for 2 minutes. The vial was sealed and the resulting solution was stirred at 100° C. for 19 h. The reaction mixture was diluted with brine, extracted with EtOAc, dried with Na2SO4 then purified by flash chromatography with a silica gel column by eluting with a mixture of Hexane:EtOAc and then further purified by preparative HPLC to give the title compound (20.7 mg). LCMS: 410.1 m/z (M+H)+; ret. Time: 3.94 (Analytical Method A).

المصدر