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To a solution of 34 μL (0.39 mmol) of methylthioacetic acid in 1 mL of methylene chloride in a ice/brine bath was added 62.8 mg (0.39 mmol) of carbonyl diimidazole. The mixture was stirred for 15 minutes and 150 mg (0.353 mmol) of [6-(6-amino-3-aza-bicyclo[3.1.0]hex-3-yl)-pyrido[3,4-d]pyrimidin-4-yl]-[3-methyl-4-(pyridin-3-yloxy)-phenyl]-amine was added along with additional methylene chloride to aid stirring. After stirring for 1 hour, the reaction was filtered and the precipitate was washed with methylene chloride and air dried. The solid was recrystallized from methanol/methylene chloride to afford 112 mg (62%) of the title compound. 1H NMR (CDCl3): δ 8.83 (s, 1), 8.35 (s, 1), 8.25 (m, 2), 7.72 (m, 1), 7.62 (m, 1), 7.24 (m, 2), 7.07 (s, 1), 6.91 (d, 1), 3.92 (d, 2), 3.52 (m, 2), 3.13 (s, 2), 2.48 (m, 1), 2.22 (s, 3), 2.10 (s, 3), 1.89 (m, 2), M.S. (m+1): 514. HPLC retention time (minutes): 5.154.

1. stirringto aid stirring
2. stirringAfter stirring for 1 hour
3. filtrationthe reaction was filtered
4. washthe precipitate was washed with methylene chloride and air
5. customdried
6. customThe solid was recrystallized from methanol/methylene chloride