Ammonium Chloride → 6-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-cyclopropyl-phenyl)-amide

Participants

Reaction Conditions

Reaction Steps

In a dried vessel, 32.8 mg (0.247 mMol) 3-cyclopropyl-aniline [preparation see: Tet. Lett. 43 (2002) 6987] are dissolved in 4.3 ml toluene and cooled to 10° C. Then 370 μl Me3Al (2 M in toluene; 0.74 mMol) are added via syringe. After 1 h at rt, a solution of 80 mg (0.247 mMol) 6-(2-methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester (Step 15.4) in 1 ml THF is added and the reaction mixture is stirred for 30 min in an oil bath of 110° C. The solution is cooled in ice and hydrolyzed with 11 ml of a sat. NH4Cl. After 15 min stirring, the mixture is diluted with EtOAc and water, the aq. phase separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; toluene/acetone 99:1→4:1) gives the title compound: MS: [M+1]+=426; TLC (toluene/acetone 4:1): Rf=0.09.

Provenance & Evidence