Chlorotrimethylsilane → HCID 18506514, compound

Participants

Reaction Steps

A mixture of compound (14) (20 g), dissopropylethylamine (74 mL), trimethylsilylchloride (21.6 mL) and 2-bromopyrimidine (Lancaster, 13.5 g) were combined in 350 mL 1,4-dioxane at room temperature, then brought to reflux under N2 atmosphere. After 2 days, an additional 12 mL silylchloride was added, and the mixture continued at reflux for an additional 2 days (until TLC showed no starting material remained). The reaction mixture was cooled to ambient temperature, concentrated to dryness in vacuo on a rotary evaporator and the residue suspended in water. The heterogeneous mixture was refluxed briefly, allowed to cool to room temperature, the product collected on a vacuum filter and air dried to give 15.3 g of (16), as a tan powder. NMR (400 MHz, DMSO-d6) d 12 (very broad, 2H) 8.3 (d, J=5 Hz, 2H) 7.7 (d, J=9 Hz, 1H), 7.28 (t, J=6 Hz, 1H), 6.57 (t, J=5 Hz, 1H), 6.49 (m, 2H), 4.13 (t, J=6 Hz, 2H), 3.62 (q, 2H); MS (+ESI) m/z 276 (M+H)+; IR (KBr) n (cm−1) 3275, 3000, 1660, 1625.

Provenance & Evidence