تفاعل #92182

معادلة التفاعل

6-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehyde

isobutylmagnesium bromide

→

6-bromo-5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

المردود 15.5%

المذيبات

THF

DCM

water

ظروف التفاعل

المعالجة

1. 1
   تجفيفThe organic layer was dried over Na2SO4
2. 2
   تركيزconcentrated to a residue which
3. 3
   أخرىwas purified by chromatography
4. 4
   غسيلeluted with PE/EA (5:1 to 1:1)

الإجراء التجريبي

To a solution of 6-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehyde (400 mg, 0.92 mmol) in THF (5 mL) was added isobutylmagnesium bromide (0.92 mL, 0.92 mmol) dropwise. The reaction was stirred at RT for 5 min then diluted with DCM (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (5:1 to 1:1) to give 6-bromo-5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (70 mg, 15.4% yield) as a solid. LCMS: MH+ 405 and TR=1.922 min.

المصدر