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Preheat oven to 375 degrees F.
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Heat medium pot over medium low heat. Melt butter. Once melted, turn heat off and add brown sugar. Use whisk to mix until well incorporated.
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Spoon one tablespoon of sugar mix into each donut pan slot and top with one slice of pineapple.
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In large mixing bowl add flour, sugar, baking powder, baking soda and salt. Mix well.
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Add buttermilk, oil, egg and pineapple juice. Mix until well combined.
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Pour donut mix into piping bag or large ziplock bag. Cut small slit on one of corners. Pipe mixture over pineapple until it's filled to top.
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Add doughnut pan to baking sheet and bake for 12-15 minutes or until toothpick inserted comes out clean.
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Remove from oven and let it cool for 10 minutes.
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Carefully remove each doughnut and add to cooling rack for another 5 minutes. Top each with one cherry and enjoy!