Reaction #76740

Reaction equation

Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-3-morpholin-4-ylmethyl-1H-indol-4-yl ester

hydrochloric acid

→

title compound

Yield 28.4%

Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-3-methyl-1H-indol-4-yl ester

Yield 28.4%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration
2. 2
   Filtrationthrough filter aid
3. 3
   Concentrationthe filtrate was concentrated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in water (10 mL)
5. 5
   FiltrationThe precipitate was collected by filtration
6. 6
   Otherpurified by preparative HPLC

Procedure

Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-3-morpholin-4-ylmethyl-1H-indol-4-yl ester (Example 10d; 270 mg, 0.55 mmol) was dissolved in methanol (50 mL) and 1 M aqueous hydrochloric acid solution (0.6 mL) and hydrogenated at room temperature and atmospheric pressure for 16 h in the presence of palladium on activated charcoal (10%, 170 mg). The catalyst was removed by filtration through filter aid and the filtrate was concentrated. The residue was dissolved in water (10 mL) and the pH set to ≈9 with 25% aqueous ammonia solution. The precipitate was collected by filtration and purified by preparative HPLC to afford the title compound (63 mg, 28%). Off-white solid.

Source