3-Furancarboxaldehyde, tetrahydro- → HCID 86651602, compound

Participants

Reaction Conditions

Reaction Steps

To 2,4-dichloropyrimidin-5-amine (6.22 g, 38.0 mmol) in 16.5 mL of dichloromethane was added dry tetrahydrofuran-3-carbaldehyde (3.8 g, 38.0 mmol). The solution was cooled to 0° C. A solution of titanium tetrachloride (41.8 ml, 41.8 mmol) in 10 mL of dichloromethane was added slowly. The reaction mixture was stirred at for 2 hours. Sodium triacetoxyborohydride (24.13 g, 114 mmol) was added in 4 equal portions over about 10 minutes and the mixture was stirred at room temperature for 48 hours. The reaction mixture was then diluted with water and extracted twice with methyl-t-butyl ether. The organic layers were combined, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 8.2 g of 2,4-dichloro-N-((tetrahydrofuran-3-yl)methyl)pyrimidin-5-amine as a tan solid which was used without further purification. [M+H] found 249.

Provenance & Evidence