Formaldehyde → 5-(4-Cyclopropylmethoxy-1-ethyl-3-morpholin-4-ylmethyl-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine

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Reaction Steps

Formaldehyde (35% aqueous solution, 41 μL, 0.48 mmol) was added at room temperature to a solution of morpholine (142 mg, 1.60 mmol) in acetic acid (1.6 mL) and water (0.2 mL). After 10 min 5-(4-cyclopropylmethoxy-1-ethyl-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine (Example 7a; 134 mg, 0.40 mmol) was added, then after 45 min the solution was concentrated. 1M aqueous sodium hydroxide solution (10 mL) was added to the viscous residue, then the suspension formed was stirred at room temperature for 1 h, the solvent was removed and the gummy precipitate washed with water and dried to afford the title compound (121 mg, 69%). Off-white solid.

Provenance & Evidence