Benzyl Bromide → 4-tert.-butyl-N-[6-(4-benzyloxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 390 mg of 4-benzyloxy-2-butyn-1-ol (prepared starting from 2-butyn-1,4-diol and benzylbromide in analogy to a procedure reported in Tetrahedron Left. 38 (1997), 7887-7890) in 5 ml DMF:THF 1:1 was added 97 mg of 55% NaH in mineral oil. After the evolution of gas had ceased, 250 mg of 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)4-pyrimidinyl]benzene sulfonamide (Example 5a) was added and the mixture was stirred at 50° C. for 20 h before it was diluted with 75 ml of ethyl acetate. The mixture was washed with 75 ml of 10% aqueous citric acid and 75 ml of water, and evaporated. The crude product was purified by chromatography on prep. tlc-plates with ethyl acetate:methanol:sat. aqueous ammonia 10:2:1 to give 125 mg of 4-tert.-butyl-N-[6-(4-benzyloxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide as a yellow foam. LC-MS: tR=5.93 min, [M+1]+=666.47, [M−1]−=664.63.

Provenance & Evidence