Sodium Hydroxide → 2-Ethynyl-6-methylpyridin-3-amine

Temperature

0 °C

(6-methyl-2-trimethylsilanylethynyl-pyridin-3-yl)amine (330 mg, 1.61 mmol) was dissolved in MeOH (3 ml) and cooled to 0° C., to the resulting solution was added 1 M solution of NaOH (1.6 ml). The ice bath was removed and the reaction mixture was stirred at room temperature for 4 h. 90 μl of acetic acid was added. The reaction mixture was partially concentrated and the residue was extracted with ethyl acetate. The organic layers were washed with water, brine, dried over Na2SO4, filtered and concentrated to yield 160 mg (1.21 mmole, 75%) of (2-ethynyl-6-methyl-pyridin-3-yl)amine as a brown solid which was used in the next step without further purification.

1. customThe ice bath was removed
2. addition90 μl of acetic acid was added
3. concentrationThe reaction mixture was partially concentrated
4. extractionthe residue was extracted with ethyl acetate
5. washThe organic layers were washed with water, brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-5774310cb4c94645917956891c84b951

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07205411B2