Diisopropylethylamine → 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine

In 4 ml of ethanol, 0.25 g of 4-carbamoyl-1,2,3,6-tetrahydropyridine trifluoroacetate and 0.35 g of 4-chloro-2,5-dimethyl-7-(isopropyl-2-methylthiophenyl)-7H-pyrrolo[2,3-d]pyrimidine were dissolved, and 0.39 g of diisopropylethylamine were added thereto. The reaction mixture was heated under reflux for 7.5 hours, and subsequently, a saturated aqueous solution of sodium hydrogencarbonate was poured into the reaction mixture. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subsequently dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform—methanol=60:1), followed by crystallization from a mixed solvent of ethyl acetate-diethyl ether to yield 0.17 g of 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine.

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 7.5 hours
3. extractionThe reaction mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialsubsequently dried over anhydrous sodium sulfate
6. filtrationAfter the desiccant was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (eluent: chloroform—methanol=60:1)
9. customfollowed by crystallization from a mixed solvent of ethyl acetate-diethyl ether

ORDレコード

ord-4cc1272895bf48348cd9913ea4d4aaf4

出典データセット

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06600038B1