반응 #351065

반응 방정식

77

6-Amino-2-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole

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79

6-Amino-2-chloro-1-(β-D-ribofuranosyl)benzimidazole

용매

NH3 MeOH

반응 조건

후처리

1. 1
   기타The reaction mixture was evaporated
2. 2
   기타coevaporated with MeOH (3×, bath temperature<40° C.)
3. 3
   기타The residue was recrystallized from MeOH

실험 절차

A solution of 0.283 g (0.665 mmole) of 77 in 10 mL of NH3 /MeOH was stirred in a pressure bottle at room temperature for 5 hr. The reaction mixture was evaporated and coevaporated with MeOH (3×, bath temperature<40° C.). The residue was recrystallized from MeOH to give 0.170 g (2 crops, 85%) of 79 as beige crystals. MP ~170° C. (dec.). MS (EI) m/e 299.0862 (16%, M+ =299.0673). 1H NMR (DMSO-d6): d 7.25 (d, 1, 4-H, J4-5 =8.5 Hz), 6.87 (d, 1, 7-H, J7-5 =2.0 Hz), 6.57 (dd, 1, 5-H), 5.75 (d, 1, 1'-H, J1'-2' =7 5 Hz), 5.43 (d, 1, 2'-OH, J2'-2'OH =6-5 Hz), 5.18 (d, 1, 3'-OH, J3'-3'OH =5.0 Hz), 5.04 (s, 2, 6-NH2), 5.03 (t, 1, 5'-OH, J5'-5'OH =5.5 Hz), 4.48 (m, 1, 2'-H, J2'-3' =6.0 Hz), 4.07 (m, 1, 3'-H, J3'-4' =3.0 Hz), 3.90 (m, 1, 4'-H, J4'-5' =4.0 Hz, J4'-5" =5.0 Hz), 3.66 (m, 2, 5'-H and 5"-H, J5'-5" =12.0 Hz). 13C NMR (DMSO-d6): d 145.34 (C6), 135.63 (C2), 134.34 (C7a), 133.18 (C3a), 118.83 (C4), 111.71 (C5), 95.79 (C7), 88.79 (C1'), 85.24 (C4'), 70.17 (C2'), 69.70 (C3'), 61.55 (C5').

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