Triethylamine → HCID 86745456, compound

Participants

Reaction Steps

(1S,4R)-4-Amino-2-cyclopentene-1-methanol dibenzoyl-D-tartrate prepared as described in Example 13 (2.76 g, 9.02 mmol) was dissolved in water (20 ml) and applied to a column of 65 ml of Amberlite IA-400 (OH- form) anion exchange resin. The column was washed with water. Basic fractions were combined and evaporated to a residual oil which was dried by evaporation of absolute ethanol and then at 0.5 mm to give oil (darkens rapidly in air) which was used immediately. This oil was dissolved in ethanol (5 ml) and added to a solution of N-(4,6-dichloro-5-formamido-2-pyrimidinyl)acetamide (2.07 g, 8.31 mmol), prepared as described in Example 15, and triethylamine (2.50 g, 24.8 mmol). The resulting dark solution was heated (oil bath 75°-80° C.) under nitrogen for 50 minutes. The solution was evaporated to a syrup which was applied to a silica gel column. Title compound was eluted with 3 to 5% methanol-chloroform as a pale yellow solid foam (1.59 g, 54%); 1H-NMR identical with that of crystallized sample. Such a sample was crystallized from ethanol to give white granules, m.p. 194°-195° C.; 1H-NMR (DMSO-d6) identical with that of the title compound of Example 15; [α]20D +2.7°, [α]54620 +2.9°, [α]43620 -2.5°, [α]36520 -41.2° (c=0.238, methanol).

Provenance & Evidence