Methane → 4-Chloro-3-ethynyl-5-nitropyridin-2-amine

To a solution of 4-chloro-5-nitro-3-((trimethylsilyl)ethynyl)pyridin-2-amine (2.36 g, 8.76 mmol) in DMF (30 mL) was added potassium fluoride on alumina (40 wt %, 3.2 g, 22 mmol). The suspension was stirred at about ambient temperature for about 2 h. Activated charcoal (0.23 g) was added and the suspension was filtered though Celite®, washed with DMF (200 mL). The solvent was removed under reduced pressure and the residue was triturated with petroleum ether (50 mL, b.p. 30-60° C.). The solid was filtered, washed with petroleum ether (4×25 mL, b.p. 30-60° C.), and dried in vacuo to give 4-chloro-3-ethynyl-5-nitropyridin-2-amine (2.12 g, 89%) as a brown solid: LC/MS (Table 1, Method c) Rt=1.32 min; MS m/z 196 (M−H)−.

1. filtrationthe suspension was filtered though Celite®
2. washwashed with DMF (200 mL)
3. customThe solvent was removed under reduced pressure
4. customthe residue was triturated with petroleum ether (50 mL, b.p. 30-60° C.)
5. filtrationThe solid was filtered
6. washwashed with petroleum ether (4×25 mL, b.p. 30-60° C.)
7. customdried in vacuo

ORD record

ord-2dfb68eb06fc45859806234c278e8e9e

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2