反応 #92170

反応方程式

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

Compound 2

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

(4-chlorophenyl)magnesium bromide

→

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

収率 51.6%

溶媒

THF

water

反応条件

後処理

1. 1
   抽出extracted with DCM (3×10 mL)
2. 2
   乾燥The combined organic layers were dried over Na2SO4
3. 3
   濃縮concentrated to a residue which
4. 4
   その他was purified by chromatography
5. 5
   洗浄eluted with PE/EA (5:1 to 1:1)

実験手順

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 (See Compound 2, Step 4, 185 mg, 0.428 mmol) in THF (5 mL) was added (4-chlorophenyl)magnesium bromide (0.77 mL, 0.772 mmol). The reaction was stirred for 5 min, diluted with water (10 mL) and extracted with DCM (3×10 mL). The combined organic layers were 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-((4-chlorophenyl) (hydroxy)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (120 mg, 51.4% yield) as a solid. LCMS: [M+-THP-OH] 441 and TR=2.021 min.

出典