HCID 9945392, compound → HCID 9923473, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [4-(2,4-Diamino-pyrimidin-5-ylmethyl)-6,7-dimethoxy-benzofuran-2-yl]-methanol (1 eq, 2.74 g, 8.3 mmol) in chloroform, Manganese oxide (10 eq, 7.22 g, 83 mmol) was added at room temperature under Argon. The reaction mixture was heated at 45° C. After completion of the reaction, the hot mixture is filtered and the manganese oxide residue is washed with hot acetonitrile. The filtrate is evaporated to give 4-(2,4-diamino-pyrimidin-5-ylmethyl)-6,7-dimethoxy-benzofuran-2-carbaldehyde as a yellow solid (1.63 g, 60%). To a suspension of 4-(2,4-diamino-pyrimidin-5-ylmethyl)-6,7-dimethoxy-benzofuran-2-carbaldehyde (1 eq, 190 mg, 0.58 mmol) and 5-fluoro-1H-indole-2-carboxylic acid methoxy-methyl-amide (2 eq, 886 mg, 1.74 mmol) in Acetic acid (C=0.20 M), a 30% solution of HBr in acetic acid (10 eq, 1.2 mL) was added slowly at 5° C. under Argon. The purple mixture was stirred 20 minutes under Argon until completion. The resulting mixture was poured onto ice water, basified to pH 8 by adding a solution saturated of NaHCO3. After centrifugation of the resulting suspension was filtered and the resulting precipitate was lyophilized overnight. The residue was then digested in methanol to precipitate the amide in excess. After filtration, the filtrate was evaporated to give the compound of formula XII. This compound was used for the next step without further purification.

Provenance & Evidence