Ethyl 4H-pyrrolo[2,3-d][1,3]thiazole-5-carboxylate → 4H-Pyrrolo[2,3-d]thiazole-5-methanol

To a solution of ethyl 4H-pyrrolo[2,3-d]thiazole-5-carboxylate (5 g, 25.48 mmol) and in anhydrous tetrahydrofuran (100 mL) was added lithium aluminum hydride (4.34 g, 127.5 mmol) dissolved in anhydrous tetrahydrofuran (50 mL) dropwise between −10° C. and 0° C. After the addition, the mixture was stirred below 0° C. for 1 hours, and then warm to the ambient temperature and allowed to stir for 3 hours at room temperature. The reaction mixture was cooled down to 0° C., quenched by 10 mL water, and then 10 mL 4N sodium hydroxide. The resulting white precipitate was filtered off, washed with acetic ester. The filtrate was dried by anhydrous sodium sulphate. The solvent was removed to afford the crude product (3.5 g, 89%). The crude product was used directly in the next step. LCMS (M+H) m/z: calcd. 154.02. found 154.9.

1. additionAfter the addition
2. stirringto stir for 3 hours at room temperature
3. temperatureThe reaction mixture was cooled down to 0° C.
4. customquenched by 10 mL water
5. filtrationThe resulting white precipitate was filtered off
6. washwashed with acetic ester
7. dry with materialThe filtrate was dried by anhydrous sodium sulphate
8. customThe solvent was removed

ORD record

ord-b6623a3d3c164173bc84998c20eb2cca

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371331B2