Tetrahydrofuran → HCID 59311650, compound

Temperature

27.5 °C

4-Bromo-1-butene (14.54 mL) was added to a mixture composed of a magnesium piece (3.17 g) and dehydrated tetrahydrofuran (150 mL) in a nitrogen atmosphere over one hour. After confirming that the internal temperature was increased, the mixture was stirred at an internal temperature of 25 to 30° C. while cooling in an ice bath for one hour to prepare a Grignard reagent. The Grignard reagent was added to a mixture composed of 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde (5.00 g) and dehydrated tetrahydrofuran (100 mL) under cooling in a dry ice-acetone bath over three hours, followed by stirring for 1.5 hours. Water (100 mL) was added to the reaction mixture, and the dry ice-acetone bath was removed. A saturated ammonium chloride solution (200 mL) was added to the reaction mixture. Then, ethyl acetate (200 mL) was added and the organic layer was separated off. The aqueous layer was extracted with ethyl acetate, and then the combined organic layers were washed with brine. The organic layers were dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure and the solvent was evaporated to obtain a crude product of the title compound (5.06 g, 78%) as a solid. The resulting compound was directly used for the next reaction without purification.

1. temperaturewas increased
2. temperaturewhile cooling in an ice bath for one hour
3. temperatureunder cooling in a dry ice-acetone bath over three hours
4. stirringby stirring for 1.5 hours
5. customthe dry ice-acetone bath was removed
6. additionA saturated ammonium chloride solution (200 mL) was added to the reaction mixture
7. additionThen, ethyl acetate (200 mL) was added
8. customthe organic layer was separated off
9. extractionThe aqueous layer was extracted with ethyl acetate
10. washthe combined organic layers were washed with brine
11. dry with materialThe organic layers were dried over sodium sulfate
12. filtrationfiltered
13. concentrationThen, the filtrate was concentrated under reduced pressure
14. customthe solvent was evaporated

ORD record

ord-318626aa03cf4adaae2d75d0f494c3c7

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158638B2