反応 #1253200

反応方程式

1 -(3,5 -Diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea hydroiodide

N-(benzyloxycarbonyloxy) succinimide

→

N-Cbz-1-(3,5-diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea

溶媒

DMF

DMF

triethylamine

反応条件

後処理

1. 1
   濃縮After this time, the reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONSilica gel (25 g) was added to the solution
3. 3
   その他the solvent was evaporated
4. 4
   その他to leave the silica gel
5. 5
   その他was purified by flash chromatography on a FlashElute™ system from Elution Solution (P.O. Box 5147, Charlottesville, Va. 22905)

実験手順

1 -(3,5 -Diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea hydroiodide (II, 494 mg, 1.27 mmol) was dissolved in a mixture of anhydrous DMF(10 mL), and triethylamine (3 mL) followed by treatment with N-(benzyloxycarbonyloxy) succinimide (470 mg, 1.7 mmol) dissolved in DMF(3 mL). The reaction mixture was stirred overnight at room temperature. After this time, the reaction mixture was concentrated under reduced pressure and the residue suspended in ethyl acetate (30 mL). Silica gel (25 g) was added to the solution and the solvent was evaporated to leave the silica gel impregnated with the crude product that was purified by flash chromatography on a FlashElute™ system from Elution Solution (P.O. Box 5147, Charlottesville, Va. 22905) using a 90 g silica gel cartridge (eluent:hexanes, ethyl acetate=1:2). The purified N-Cbz-1-(3,5-diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea (III) was yield);1H NMR (360 MHz, DMSO-d6) δ2.33 (s, 3H), 2.61 (s, 3H), 4.99 (s, 2H), 7.39 (m, 10H), 13.7 (s, 1H); API MS m/z=395 [C15H15ClN6O3S+H]30; LC/MS (Method A)>99%, tr=10.1 min.

出典