2,1,3-Benzothiadiazol-5-amine → 2-(2,1,3-benzothiadiazol-5-ylamino)-8-cyclopentyl-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one

Participants

Reaction Steps

202 mg of potassium tert-butoxide are added in 3 installments, at ambient temperature under argon, to 500 mg of compound of formula (II), 8-cyclopentyl-6-(2,6-dichlorophenyl)-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, and 249 mg of the compound of formula (III), 2,1,3-benzothiadiazol-5-ylamine, in suspension in 18 ml of DMSO. After a contact time of 45 min, the reaction medium is diluted with a mixture of water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are then washed with water and then with a saturated NaCl solution. After drying over sodium sulfate and filtering, the residue is chromatographed on silica (gradient: heptane 100 to heptane/ethyl acetate 60:40) and precipitated from diethyl ether to give 283 mg of the expected product in the form of a yellow solid.

Provenance & Evidence