Diisopropylamine → 3-Ethynyl-6-methoxymethyl-pyridin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of diisopropylamine (0.15 mL) and THF (2 mL) was added n-butyl lithium (1.6M n-hexane solution, 0.68 mL) by drops at −78° C., which was stirred for 30 minutes at the same temperature. Trimethylsilyldiazomethane (2M n-hexane solution, 0.50 mL) was added to the reaction mixture at −78° C., which was stirred for 30 minutes at the same temperature. 2-Amino-6-methoxymethyl-pyridin-3-carbaldehyde (150 mg) described in Manufacturing Example 19-2 and THF (1.5 mL) were added by drops to the reaction mixture at −78° C., which was stirred for 30 minutes at 0° C. The reaction mixture was cooled to −78° C., after which a mixture of acetic acid (0.10 mL) and THF (1 mL) was added by drops thereto. The reaction mixture was gradually raised to 0° C., and was extracted using water and ethyl acetate. The organic layer was washed with saturated brine and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=2:3) to obtain the titled compound (73 mg).

Provenance & Evidence