反应详情

温度

0 °C

To an ice-cooled solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol (1.90 g, 12.02 mmol) in THF (60 mL), NaH (673 mg, 16.82 mmol, 60%) was added and the solution was stirred for 5 min at 0° C., then the ice bath was removed and the reaction mixture was stirred at rt for 30 min, before 2-chloro-4,6-dimethoxypyrimidine (2.31 g, 13.22 mmol) was added. After 40 min at rt, the reaction mixture was quenched with water and the org. solvent was removed in vacuo. The aq. layer was extracted with DCM (1×), then acidified with 1 N HCl-solution to pH 2, and extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent removed under reduced pressure. Purification by crystallization (DCM-hept-mixture) yielded 4,6-dimethoxy-2-(2-(4-nitro-1H-pyrazol-1-yl)ethoxy)pyrimidine as a beige solid. LC-MS conditions A: tR=0.88 min, [M+H]+=295.98.

1. additionwas added
2. customthe ice bath was removed
3. additionwas added
4. waitAfter 40 min at rt
5. customthe reaction mixture was quenched with water
6. customsolvent was removed in vacuo
7. extractionThe aq. layer was extracted with DCM (1×)
8. extractionextracted with DCM (2×)
9. washlayers were washed with brine
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. customthe solvent removed under reduced pressure
13. customPurification
14. customby crystallization (DCM-hept-mixture)