He was signed by the Red Sox as an international free agent on July 2, 2006 as a 16-year-old by then Boston Scout Luis Scheker. He made his debut the next season with the DSL Red Sox, going 3-1 with a 2.90 ERA in 13 starts. He made the trip to America for the 2008 season, playing it with Low-A Lowell, going 5-2 with a 3.14 ERA in 11 starts. He played 2009 with Single-A Greenville, going 10-7 with a 3.82 ERA in 23 starts. He played 2010 with High-A Salem going 9-11 with a 4.06 ERA in 26 starts. Despite the worst season of his short career, he was nominated to the All-Star Futures Game facing 2 batters, Logan Morrison and Danny Espinosa, retiring them both. In the offseason, Pimentel signed a one-year, $414,000 deal, protecting him from the Rule V Draft. He started 2011 with Double-A Portland, but he went 0-9 with a 9.12 ERA in 15 starts, leading to a demotion back to Salem. He finished the season 6-13 with a 6.79 ERA in 25 starts.\n', '

On December 26, 2012 the Red Sox traded him (along with Mark Melancon, Jerry Sands and Iván DeJesús, Jr.) to the Pittsburgh Pirates for Brock Holt and Joel Hanrahan. He made his MLB debut on September 4, 2013 for the Pirates. He pitched out of the bullpen, and made five appearances in 2013. Pimentel started the 2014 season on the Pirates Opening Day roster.\n', '

Pimentel was designated for assignment by the Pirates on April 5, 2015.\n', '

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