Sodium Hydroxide → Dimethyl-sulfamic Acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-1H-indol-4-yl ester

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Reaction Steps

Tetrabutylammonium bromide (61 mg, 0.19 mmol) and 50% aqueous sodium hydroxide solution (7.8 mL) were added to a suspension of 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-1H-indol-4-ol (Example 6; 436 mg, 1.54 mmol) in dichloromethane (130 mL), and the mixture was vigorously stirred for 15 min. Dimethylsulfamoyl chloride (226 mg, 1.57 mmol) was added, then after 2 h another portion of dimethylsulfamoyl chloride (60 mg, 0.42 mmol) was added. After 16 h the reaction mixture was partitioned between dichloromethane (130 mL) and water (50 mL), the organic layer was washed with brine, dried (MgSO4), and evaporated. The crude product was purified by preparative HPLC to afford the title compound (51 mg, 9%). Light brown solid.

Provenance & Evidence