Benzyl Alcohol → 2-benzyloxy-4,6-dichloro-[1,3,5]triazine

First, a synthesis method of the hydroxy group-protecting agent 3 will be explained. An activated molecular sieve 4A, 54.1 μL (0.525 m mol) of benzyl alcohol, 118.9 mg (0.600 m mol) of 1,10-phenanthroline hydrate, 1.00 mL of dichloromethane, 92.2 mg (0,500 m mol) of cyanuric chloride were added to a test tube, and reacted at 0 degree under a nitrogen atmosphere for 5 hours. After the reaction, a precipitate was filtered, and 20 mL of ethyl acetate was added to the filtrate, which was washed with 10 mL of an aqueous solution of saturated sodium hydrogen carbonate, 5 mL of water, 10 mL of 1 N hydrochloric acid, 5 mL of water and 10 mL of saturated salt water. A resulting organic phase was dried by magnesium sulfate, from which ethyl acetate was distilled away, and the residue was isolated and purified by silica-gel chromatography to obtain 58.9 mg of 6-benzyloxy-2,4-dichloro-1,3,5-triazine (yield: 46%).

1. customreacted at 0 degree under a nitrogen atmosphere for 5 hours
2. customAfter the reaction
3. filtrationa precipitate was filtered
4. addition20 mL of ethyl acetate was added to the filtrate, which
5. washwas washed with 10 mL of an aqueous solution of saturated sodium hydrogen carbonate, 5 mL of water, 10 mL of 1 N hydrochloric acid, 5 mL of water and 10 mL of saturated salt water
6. dry with materialA resulting organic phase was dried by magnesium sulfate, from which ethyl acetate
7. distillationwas distilled away
8. customthe residue was isolated
9. custompurified by silica-gel chromatography

ORD record

ord-58a26a68a85441e08ffc661b3480469e

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126954B2