Реакция #73296

Уравнение реакции

1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate

4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

sodium hydride

→

4-[1-(1,4-Dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураto warm to 25° C.
2. 2
   Температураwas then heated to 55° C. for 24 hours
3. 3
   ЭкстракцияThe reaction was then extracted with ethyl acetate
4. 4
   ПромывкаThe organic extracts were washed with water and saturated NaCl
5. 5
   Сушкаdried (MgSO4)
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   ДругоеThe concentrate was chromatographed on silica gel using 1:1 EtOAc/hexanes
8. 8
   Другоеto give the product

Методика

A mixture of 1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate (0.50 g, 0.0015 mol) with 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (0.36 g, 0.0011 mol) and sodium hydride (0.082 g, 0.0020 mol) was cooled at −78° C. and DMF (2.0 mL) was added. The reaction was allowed to warm to 25° C. and was then stirred for 20 minutes and was then heated to 55° C. for 24 hours. The reaction was then extracted with ethyl acetate. The organic extracts were washed with water and saturated NaCl, then dried (MgSO4) and concentrated in vacuo. The concentrate was chromatographed on silica gel using 1:1 EtOAc/hexanes to give the product. LC/MS (M+H)+: 456, 1H NMR(CDCl3): 8.89 (s, 1H), 8.35 (s, 1H), 8.30 (s, 1H), 7.44 (d, 1H), 6.87 (d, 1H), 5.73 (s, 2H), 4.38 (m, 1H), 4.06 (s, 4H), 3.60 (m, 2H), 2.22-2.31 (m, 4H), 2.00 (m, 2H), 1.86 (m, 2H), 0.98 (m, 2H), 0.00 (s, 9H)

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