Triethylamine → 4-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acid

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Reaction Steps

A solution of 2.21 g (11.45 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid prepared in step 2.3 (method B) in 20 mL of anhydrous THF is cooled to 2-5°C. on an ice bath. A solution of 4.79 mL (34.35 mmol) of triethylamine and 2 g (11.48 mmol) of tert-butyl (3-aminopropyl)carbamate in 15 mL of anhydrous THF is then added dropwise. The reaction mixture is stirred at room temperature for 30 minutes. Ethyl acetate is added and the organic phase is washed with aqueous 1N HCl and with water. The organic phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum. 3.35 g of the expected product are obtained in the form of a yellow solid. Yield=88.6%.

Provenance & Evidence