2-Butyne-1,4-diol → HCID 10233725, compound

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Reaction Steps

Crude 4-tert.-butyl-N-[6-(4-(3-methoxybenzyloxy)-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide was obtained starting from 300 mg of 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide (Example 5a) and 1096 mg of 4-(3-methoxybenzyloxy)-2-butyn-1-ol (prepared starting from 2-butyn-1,4-diol and 3-methoxybenzylbromide in analogy to a procedure reported in Tetrahedron Lett. 38 (1997), 7887-7890) following the procedure given in Example 91. The compound was purified by column chromatography on silica gel eluting with DCM containing 0-2.5% of methanol followed by chromatography on prep. tlc-plates with DCM containing 5% of methanol. The resulting oil was dissolved in 10 ml of diethyl ether and treated with pentane. The precipitate was collected and dried to give 102 mg of 4-tert.-butyl-N-[6-(4-(3-methoxybenzyloxy)-2-butynyloxy)-5-(o-methoxy-phenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide as an almost white powder. LC-MS: tR=5.74 min, [M+1]+=696.40, [M−1]−=694.32.

Provenance & Evidence