6-Aminobenzothiazole → Benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochloride

Participants

Reaction Conditions

Reaction Steps

Alternative preparation: A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (5.02 g, 15 mmol) and 1,3-benzothiazol-6-amine (2.25 g, 15 mmol) in 1-butanol (50 mL) was heated at 115° C. overnight, LC-MS showed the desired product and some de-Boc product. After the mixture was cooled to rt, it was diluted with hexane (50 mL), the gray solid was collected by filtration, a mixture of the desired product and some de-Boc product, which was directly used in the next step. To a suspension of this material in methylene chloride (30 mL) was added 4M HCl/1,4-dioxane (30 mL), the resulting mixture was stirred at rt for 5 h. The mixture was then diluted with CH2Cl2 (30 mL), and the light-yellow solid was collected by filtration and dried in vacuo.

Provenance & Evidence