Ammonium Chloride → (1H-Thieno[3,2-c]pyrazol-5-yl)methanol

To a solution of methyl 1-acetyl-1H-thieno[3,2-c]pyrazole-5-carboxylate (F-5) (4.5 g, 20.0 mmol) in MeOH (30 mL) was slowly added NaBH4 (836 mg, 22.0 mmol). The mixture was stirred at room temperature for 30 mins, and then concentrated. The residue was dissolved in anhydrous THF (80 mL) and then LiAlH4 (1.5 g, 40.0 mmol) was slowly added at 0° C. The reaction mixture was stirred at 0° C. for 30 min. Aqueous NH4Cl solution was added dropwise to quench the reaction. The resulting mixture was filtered, and the filtrate was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give the title compound (2.9 g).

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in anhydrous THF (80 mL)
3. stirringThe reaction mixture was stirred at 0° C. for 30 min
4. customto quench
5. customthe reaction
6. filtrationThe resulting mixture was filtered
7. extractionthe filtrate was extracted with ethyl acetate
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo

ORD record

ord-82ebeb4c9cac406bb41373bc503c47fe

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507487B2