反応 #1973955

反応方程式

1-tert-butyl-3,5-diiodo-2-methoxybenzene

Uracil

K3PO4

N-(2-cyanophenyl)picolinamide

→

product

収率 70.0%

1-(3-tert-Butyl-5-iodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

収率 70.0%

溶媒

MeCN

DMSO

反応条件

後処理

1. 1
   その他sparged with argon
2. 2
   workup.ADDITIONadded to the solids
3. 3
   温度After cooling
4. 4
   workup.ADDITIONthe reaction was diluted with 2 L EtOAc
5. 5
   洗浄washed with 2.6 L water (
6. 6
   抽出back extracted with 3×1 L EtOAc)
7. 7
   洗浄The combined organic layers were washed with 2×1 L of 0.25M (CuOAc)2
8. 8
   濃縮The organic layer was then concentrated
9. 9
   その他triturated
10. 10
    温度with refluxing 85:15 (v/v) heptane
11. 11
    温度After cooling
12. 12
    ろ過the product was collected by filtration
13. 13
    洗浄washed with an additional 330 mL of 85:15 v/v heptanes
14. 14
    その他EtOAc to yield

実験手順

Uracil (33.3 g, 297 mmol, 1.2 equiv.), K3PO4 (106 g, 500 mmol, 2.1 equiv.), CuI (4.6 g, 24.2 mmol, 0.1 equiv.), and N-(2-cyanophenyl)picolinamide (6.4 g, 28.7 mmol, 0.12 equiv.) were charged to a flask and inerted with argon. The 1-tert-butyl-3,5-diiodo-2-methoxybenzene was solvent switched into MeCN, dissolved in 1 L DMSO and sparged with argon and added to the solids. The reaction was heated to 60° C. for 16 h. After cooling, the reaction was diluted with 2 L EtOAc and washed with 2.6 L water (back extracted with 3×1 L EtOAc). The combined organic layers were washed with 2×1 L of 0.25M (CuOAc)2 then 2×830 mL 15% NH4Cl then 800 mL brine. The organic layer was then concentrated and chased with 1 L heptane, then triturated with refluxing 85:15 (v/v) heptane:iPrOAc for 4 h. After cooling, the product was collected by filtration and washed with an additional 330 mL of 85:15 v/v heptanes:EtOAc to yield after drying 66.9 g (70% yield) of the product as a white solid.

出典