1,1-Dimethoxyethane → HCID 18328131, compound

Participants

Reaction Conditions

Reaction Steps

Isonicotinamidine hydrochloride (5.00 g, 31.7 mmol) and acetaldehyde dimethylacetal (8.44 mL, 63.5 mmol) were combined and heated to 110° C. in anhydrous DMF (35 mL) in the presence of DBU (14.20 mL, 95.2 mmol) for 3 h. The reaction mixture was cooled to 20° C., then stirred for 16 h, before being concentrated in vacuo. The residue was partitioned between H2O (100 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (2×50 mL), then the combined organics were washed with brine (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Flash column chromatography (EtOAc) of the residue gave 4-methyl-2-pyridin-4-yl-pyrimidine: δH ((CD3)2SO): 2.57 (3H, s), 7.45 (1H, d), 8.21-8.26 (2H, m), 8.72-8.77 (2H, m), 8.82 (1H, d). To a solution of this compound (1.06 g, 6.17 mmol) in anhydrous dioxane (20 mL) was added SeO2 (2.05 g, 18.51 mol), then the mixture was heated to reflux for 90 h. The reaction mixture was cooled to 20° C. then filtered, washing with EtOAc. The filtrate was evaporated to dryness, then the residue was suspended in CH2Cl2. The suspension was filtered, washing with CH2Cl2, then the filtrate was evaporated to dryness to furnish the title compound: δH (CDCl3): 7.80 (1H, d), 8.38 (2H, d), 8.83 (2H, d), 9.13 (1H, d), 10.15 (1H, s).

Provenance & Evidence