Methanol → 3-(but-3-ynyl)-5-tert-butylthiazol-2(3H)-imine

A mixture of the product of Example 74A (0.20 g, 1.3 mmol), the product of Example 78A (0.29 g, 1.3 mmol), tetrabutylammonium iodide (0.24 g, 0.64 mmol) in DMF (1.5 mL) was warmed to 85° C. and stirred for 16 h. The mixture was cooled to ambient temperature and quenched with saturated aqueous NaHCO3 (5 mL) and diluted with EtOAc (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 10% MeOH in EtOAc then 9:1:0.1 CH2Cl2:MeOH:NH4OH) to provide the title compound (0.18 g, 0.84 mmol, 65% yield). MS (DCI/NH3) m/z 209 (M+H)+.

1. customquenched with saturated aqueous NaHCO3 (5 mL)
2. additiondiluted with EtOAc (10 mL)
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
5. dry with materialThe combined organics were dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. custompurified via flash column chromatography (SiO2, 10% MeOH in EtOAc

ORDレコード

ord-4fb9707570334bf29c1de23db284c926

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07875640B2