反应详情

To a stirred solution of [2-chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-cyclopentyl-amine (7.50 g, 23.3 mmol) in THF (45 mL) is added IN TBAF in THF (100 mL, 116 mmol) at room temperature. The reaction mixture is heated under reflux overnight. After cooling the mixture is partitioned between H2O and dichloromethane. The phases are separated and the aqueous layer is extracted with dichloromethane (×2). The combined organic extracts are dried (MgSO4), filtered and concentrated. The residue is purified by SiO2 chromatography eluting with a gradient of 10% EtOAc/petrol to 30% EtOAc/petrol to give 2-chloro-7-cyclopentyl-6-diethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine, (5.68 g, 76%). MS (ESI) m/z 324.1 (M+H)+

1. temperatureThe reaction mixture is heated
2. temperatureunder reflux overnight
3. temperatureAfter cooling the mixture
4. customis partitioned between H2O and dichloromethane
5. customThe phases are separated
6. extractionthe aqueous layer is extracted with dichloromethane (×2)
7. dry with materialThe combined organic extracts are dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue is purified by SiO2 chromatography
11. washeluting with a gradient of 10% EtOAc/petrol to 30% EtOAc/petrol