Triethylamine → N-{3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5-{2-[2-(methylthio)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine

The compound (150 mg) of Example 147 was dissolved in tetrahydrofuran (10 mL) and triethylamine (1.50 mL) and methanesulfonyl chloride (0.70 mL) were added under ice-cooling, and the mixture was stirred for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to this reaction solution under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated, and the residue was dissolved in a mixed solvent of N,N-dimethylformamide (5.0 mL) and tetrahydrofuran (4.0 mL). Sodium methanethiolate (180 mg) was added, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=90:10) to give the title compound (123 mg).

1. temperaturecooling
2. temperaturecooling
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialThe extract was dried over magnesium sulfate
5. concentrationconcentrated
6. dissolutionthe residue was dissolved in a mixed solvent of N,N-dimethylformamide (5.0 mL) and tetrahydrofuran (4.0 mL)
7. additionSodium methanethiolate (180 mg) was added
8. stirringthe mixture was stirred at room temperature for 1 hr
9. additionSaturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-
10. temperaturecooling
11. extractionthe mixture was extracted with ethyl acetate
12. dry with materialThe extract was dried over magnesium sulfate
13. concentrationconcentrated
14. customThe residue was separated
15. custompurified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=90:10)

ORDレコード

ord-d18b08867cbf45af870f34b2c85c38e0

出典データセット

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08178543B2