반응 #720966

반응 방정식

compound 10

4-Chloro-5-iodo-7-(2-C-methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

ammonia

→

title compound 6

수율 69.0%

4-Amino-5-iodo-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

수율 69.0%

용매

dioxane

반응 조건

후처리

1. 1
   온도After cooling the volatiles
2. 2
   기타were evaporated
3. 3
   기타crude product was purified by chromatography on silica (CHCl3→CHCl3MeOH, 8:2)
4. 4
   기타re-purified by reverse phase chromatography (0→100% MeOH in water)

실험 절차

A mixture of compound 10 from Step 1 (200 mg, 0.27 mmol) and aq ammonia (25% w/w, 3 ml) in dioxane (3 ml) was stirred in a sealed tube at 120° C. for 10 h. After cooling the volatiles were evaporated and crude product was purified by chromatography on silica (CHCl3→CHCl3MeOH, 8:2) and then re-purified by reverse phase chromatography (0→100% MeOH in water) to afford title compound 6 as white solid (76 mg, 69%). Compound was recrystallized from MeOH/MeCN. Mp 207° C. [α]20D −39.0 (c 0.274, MeOH). 1H NMR (600 MHz, DMSO-d6): 0.67 (s, 3H, CH3); 3.65 (ddd, 1H, Jgem=12.1, J5′b,OH=4.8, J5′b,4′=2.7, H-5′b); 3.81 (ddd, 1H, Jgem=12.1, J5′a,OH=4.8, J5′a,4′=2.0, H-5′a); 3.79 (ddd, 1H, J4′,3′=9.1, J4,5=2.7, 2.0, H-4′); 3.93 (bd, 1H, J3′,4′=9.1, H-3′); 5.14 (s, 1H, OH-2′); 5.16 (bs, 1H, OH-3′); 5.22 (t, 1H, JOH,5′=4.8, OH-5′); 6.10 (s, 1H, H-1′); 6.67 (bs, 2H, NH2); 7.82 (s, 1H, H-6); 8.10 (s, 1H, H-2). 13C NMR (151 MHz, DMSO-d6): 19.89 (CH3); 51.68 (C-5); 59.46 (CH2-5′); 71.76 (CH-3′); 78.87 (C-2′); 82.39 (CH-4′); 90.71 (CH-1′); 103.11 (C-4a); 126.81 (CH-6); 149.88 (C-7a); 152.23 (CH-2); 157.43 (C-4). IR (Mk): 3474, 3429, 3392, 3366, 1631, 1582, 1553, 1504, 1440, 1343, 1295, 1147, 1128, 1070, 1045, 789. MS (FAB): m/z 407 (M+H). HRMS (FAB) for C12H16H4O4 [M+H] calcd: 407.0216. found: 407.0225. Anal. Calcd for C12H15IN4O4: C, 35.48; H, 3.72; N, 13.79. Found: C, 35.37; H, 3.72; N, 13.39.

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