Hydrochloric Acid → HCID 11824456, compound

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Reaction Steps

A mixture of 1.22 g of TMEDA and 60 ml of THF is prepared under anhydrous condition and cooled to -10° with stirring. 36.03 g of a 20.5% solution of n-BuLi in cyclohexane is added and after 30 mins stirring the solution is cooled to -60°. A solution of 10.0 g of 2,5-dichlorobenzoic acid in 40 ml of THF is added over 10 min. at -60°. After a further 30 mins of stirring this solution is added over 15 min under argon pressure to a solution of 8.97 g of allyl 4,6-dimethoxypyrimidine-2-carboxylate in 60 ml of THF at -25° and the clear yellow solution cooled to -25°. After stirring at -20° for 60 mins, 60 ml of 10% HCl are added and the temperature allowed to rise to 13° with stirring over a 15 min period. The organic phase is separated and evaporated to yield a viscous residue to which is added 17 ml of methanol. The resulting suspension is cooled in an ice/water bath, filtered and the crystals washed with 2×10 ml methanol and dried under vacuum at 70° C. to yield the title product.

Provenance & Evidence