Sodium hydride → 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-octyl-1,2,4-oxadiazol-5-yl)pyrimidine

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Prepared by a procedure similar to Example 9, where sodium hydride (60% dispersion in mineral oil 104 mg, 2.6 mmol) and n-nonanamidoxime (448 mg, 2.6 mmol) were suspended in dry THF in an oven dried round bottom flask with stirring under nitrogen at 0° C. After 15 minutes stirring the ice bath was removed and the grey suspension refluxed 45 minutes to give a white suspension. 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-methoxycarbonylpyrimidine (1.0 g, 2.6 mmol) was added dissolved in dry THF and reflux continued 18 hours. The solvents were evaporated in vacuo and the residue was chromatographed (silica, chloroform/methanol, 9:1) to yield 1-triphenylmethyl-1,4,5,6-tetrahydro-5-(3-octyl-1,2,4-oxadiazol-5-yl)pyrimidine 780 mg (60%). This product was dissolved in triflouroacetic acid (2 ml), with stirring at room temperature for 24 hours. The yellow solution was then evaporated in vacuo, and the residue recrystallized from methanol/ether to yield 182 mg (30%) white crystals, mp 97°-99° C. identified by 300 MHz nmr.

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