反応 #88765

反応方程式

1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

H2O2

→

6-hydroxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

収率 100.0%

溶媒

MeOH

反応条件

後処理

1. 1
   その他quenched with aq. 1M Na2SO3 solution (100 mL)
2. 2
   workup.STIRRINGstirred for 15 min
3. 3
   抽出then extracted with EA (3×75 mL)
4. 4
   乾燥The combined organic layers were dried over Na2SO4
5. 5
   濃縮concentrated

実験手順

To a solution of 1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (2.8 g, 6.3 mmol) in MeOH (100 mL) at 0° C. was added H2O2 (30% in water, 1.4 mL, 10.6 mmol) dropwise over 5 min. The reaction was allowed to warm slowly to RT, stirred for 16 h, quenched with aq. 1M Na2SO3 solution (100 mL), stirred for 15 min then extracted with EA (3×75 mL). The combined organic layers were dried over Na2SO4 and concentrated to give a residue of 6-hydroxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (2.1 g, 100% yield) as a solid. LCMS: [MH+-THP] 252 and TR=1.740 min. Used without further purification.

出典