Реакция #358796

Уравнение реакции

6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

1-oxa-8-thia-3-aza-spiro[4.5]decane-2,4-dione

K2CO3

→

7-(2,2-dimethyl-propyl)-6-(2,4-dioxo-1-oxa-8-thia-3-aza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Выход 39.5%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеthe reaction mixture is quenched with H2O
2. 2
   Экстракцияextracted with AcOEt
3. 3
   ПромывкаThe combined extracts are washed with brine
4. 4
   Сушкаdried over MgSO4
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe residue is purified by reverse-phase HPLC

Методика

To a solution of 200 mg (0.52 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile and 146 mg (0.78 mmoles) of 1-oxa-8-thia-3-aza-spiro[4.5]decane-2,4-dione in 5 ml of DMF, 117 mg (0.846 mmoles) of K2CO3 is added at ambient temperature. After being stirred for 18 hours, the reaction mixture is quenched with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by reverse-phase HPLC to give 85 mg of disired 7-(2,2-dimethyl-propyl)-6-(2,4-dioxo-1-oxa-8-thia-3-aza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (NVP-TAB516-NX) in 32% yield.

Источник