反応 #162592

反応方程式

NEt3

2,4,6-Trichloropyrimidine

2,4,6-trichloropyrimidine

8-Oxa-3-aza-bicyclo[3.2.1]octane hydrochloride

8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride

→

3-(2,6-dichloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane

収率 83.0%

3-(2,6-Dichloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane

収率 83.0%

3-(4,6-dichloro-pyrimidin-2-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane

収率 11.0%

溶媒

EtOH

反応条件

後処理

1. 1
   濃縮The mixture was concentrated
2. 2
   workup.DISSOLUTIONdissolved in EtOAc
3. 3
   洗浄washed with saturated NaHCO3
4. 4
   抽出The aqueous phase was extracted with EtOAc the combined organic phases
5. 5
   乾燥were dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The mixture was purified by silica gel chromatography (10-80% EtOAc in hexanes)

実験手順

2,4,6-Trichloropyrimidine (8, 6.325 mL, 55 mmol) was dissolved in 220 mL EtOH at 0° C. 8-Oxa-3-aza-bicyclo[3.2.1]octane hydrochloride (2, 8.23 g, 55 mmol) was added followed by the addition of NEt3 (23.1 mL, 165 mmol). The mixture was allowed to warm to room temperature and stirred for 1 hour at ambient temperature. The mixture was concentrated, dissolved in EtOAc and washed with saturated NaHCO3. The aqueous phase was extracted with EtOAc the combined organic phases were dried (MgSO4), filtered, and concentrated. The mixture was purified by silica gel chromatography (10-80% EtOAc in hexanes) to give 11.807 g (45 mmol, 83%) of 3-(2,6-dichloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (9) along with 1.631 g (6.2 mmol, 11%) of 3-(4,6-dichloro-pyrimidin-2-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (10).

出典