Hydrazine → 2-Chloro-4-hydrazinyl-5-methoxypyrimidine

温度

43 °C

Anhydrous sodium carbonate (29.15 g, 0.275 mole), methanol (300 mL), and 35% aqueous hydrazine (54.9 g, 0.60 mole) were loaded into a 1 L glass jacketed reactor equipped with a thermocouple temperature probe, overhead stirrer with glass agitator, condenser, and a programmable circulating bath. 2,4-Dichloro-5-methoxypyrimidine (89.50 g, 0.50 mole) was added as a solid in small increments over 70 min. During the addition, the reactor jacket was kept at 20° C., and the reaction temperature rose from 21° C. to 28° C. Upon completion of the addition, the reaction mixture was heated to 43° C. over 60 min, then held at 43° C. for 4.5 h. Water (300 mL) was then added, and a distillation head was attached to the reactor. Vacuum was applied to lower the pressure to 140 mmHg, and methanol was removed by distillation. Distillation continued for 1.5 h, at which point the rate of distillation had slowed greatly. The pressure as further decreased to 85 mmHg until water started to distill over, then vacuum was broken under a nitrogen flow. The reaction mixture was cooled from 43° C. to 25° C. over 60 min. The resulting slurry was stirred overnight at 25° C. The product was recovered by filtration through Whatman #52 filter paper using a Buchner funnel and aspirator vacuum. After washing the filter cake with water (221 g), the product was dried overnight in vacuo at 42° C., to give 83.5 g of white 2-chloro-4-hydrazino-5-methoxypyrimidine (purity 96.8%, yield=92.7%).

1. customequipped with a thermocouple temperature probe, overhead stirrer with glass agitator, condenser
2. additionDuring the addition
3. customwas kept at 20° C.
4. customrose from 21° C. to 28° C
5. additionUpon completion of the addition
6. customwas removed by distillation
7. distillationDistillation
8. waitcontinued for 1.5 h, at which point
9. distillationthe rate of distillation
10. distillationto distill over, then vacuum
11. temperatureThe reaction mixture was cooled from 43° C. to 25° C. over 60 min
12. filtrationThe product was recovered by filtration through Whatman #52
13. filtrationfilter paper
14. washAfter washing the filter cake with water (221 g)
15. customthe product was dried overnight in vacuo at 42° C.

ORDレコード

ord-727c212fc5d6468e8b3bebfacbedc457

出典データセット

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06362335B1