Triethylamine → HCID 86726549, compound

Participants

Reaction Steps

Add a solution of 3-chloropropyl carbonochloridate (0.55 mL; 1.2 equiv; 4.51 mmoles) in tetrahydrofuran (25 mL) over 1 hour to a mixture of N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (1.00 g; 1.0 equiv; 3.75 mmoles) and triethylamine (1.10 mL; 2.1 equiv; 7.88 mmoles) in tetrahydrofuran (25 mL). Stir for 2 hours, then dilute with dichloromethane and saturated sodium bicarbonate and separate the layers. Further extract the aqueous layer with dichloromethane (2×). Dry the combined organic extracts over sodium sulfate, filter, and concentrated to dryness to give a yellow oil. Purify the crude product by column chromatography (10% methanol in dichloromethane) to 3-chloropropyl 2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylate (1.146 g; 79%): MS (m/z): 387(M+1).

Provenance & Evidence