((2R)-2-(Cyclopentylmethyl)-3-{2-[2-ethyl-5-fluoro-6-(4-methyl-1-piperazinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide → ((2R)-2-(Cyclopentylmethyl)-3-{2-[2-ethyl-5-fluoro-6-(4-methyl-1-piperazinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide

Participants

Reaction Steps

A mixture of ((2R)-2-(cyclopentylmethyl)-3-{2-[2-ethyl-5-fluoro-6-(4-methyl-1-piperazinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide (17.1 g, 31.61 mmol) and 10% Pd/C (4 g) suspended in MeOH (400 mL) was stirred under a balloon of H2 gas. After 2 h, and additional 2 g of fresh 10% Pd/C was added. The resulting suspension was stirred for another 1.5 h under a hydrogen atmosphere until the staring material was consumed. The Pd/C was removed by filtration through Celite, washing with MeOH and CH2Cl2. The filtrate was concentrated in vacuo. As the evaporation proceeded, the product crystallized out from the remaining solution. The evaporation continued until only ˜50 mL of liquid remained. The crystals were then collected by filtration to provide the product as a white solid (10.0 g). The filtrate was further evaporated to give a second crop of crystals (1.5 g) as the pure product. In the same way, a third crop was collected. The combined yield of ((2R)-2-(cyclopentylmethyl)-3-{2-[2-ethyl-5-fluoro-6-(4-methyl-1-piperazinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide was 86% (12.2 g). LCMS: (M+H)+: 452.1.

Provenance & Evidence