| 75% | With bis(isopropyl)ethylamine; In propan-1-ol; at 80℃; for 6h; | A mixture of <strong>[27757-86-4]3-(aminomethyl)thiophene</strong> (0.25 mL, 2.5 mmol), 6-chloropurine ribofuranoside (143 mg, 0.5 mmol), and diisopropylethylamine (2 mL, 12 mmol) in 1-propanol (25 mL) was heated at 80 C for 6 h. The mixture was concentrated by rotary evaporation, and recrystallized from MeOH to yield the desired product JMF3461 (136 mg, 75% yield). The purity of product was 99% as shown by HPLC on an HC-C18 column (Agilent, 4.6 chi 250 mm, 5 mutaueta) with elution of gradients of 50% aqueous MeOH. C15Hi7504S; yellow powder; mp 134.3-135.1 C; [a]2D= -58.6 (DMSO, c = 1.0); TLC (2-propanol/hexane, (2:3)) R = 0.33; 1H NMR (DMS0-4s, 400 MHz) 6 8.36 (2 H, br s), 8.22 (1 H, s), 7.43 (1 H, dd, J= 3, 5 Hz), 7.28 (1 H, d, J= 1.6 Hz), 7.09 (1 H, d, J= 4.8 Hz), 5.88 (1 H, d, J = 6.4 Hz), 5.43 (1 H, d, J= 6.0 Hz), 5.38 (1 H, q, J= 4.6 Hz), 5.17 (1 H, d, J= 4.4 Hz), 4.69 (2 H, s), 4.63^1.16 (1 H, m), 4.14-4.13 (1 H, m), 3.97-3.95 (1 H, m), 3.69-3.64 (1 H, m), 3.57-3.52 (1 H, m),13C NMR (DMSO-i/<s, 100 MHz) delta 154.4, 152.3, 148.5, 140.8, 139.9, 127.9, 125.1, 120.0, 1 19.8, 87.9, 85.9, 73.5, 70.7, 61.7, 42.9; ESI-MS calcd for CuH^NjC^S: 364.1080, found: m/z 364.1079 [M + H]+. |
| With triethylamine; In propan-1-ol; at 70℃; for 8h; | First step, hydroxyamine hydrochloride (874 mg) and NaOAc (1.18 g) were added to a solution of 3-thiophenecarbaldehyde (800 mg) in EtOH (50 ml). The reaction mixture was stirred at room temperature for 6 h. EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 3-thiophenecarbaldehyde oxime (722 mg) as a pale yellowish solid. Second step, 3-thiophenecarbaldehyde oxime (722 mg) and zinc dust (2.23 g) in HOAc (5 ml) was stirred at room temperature for 6 h. The reaction solution was filtered to remove the excess zinc dust and ZnOAc residue, and the filtrate was concentrated to yield 3-thiopheneylmethanamine (323 mg) as a yellowish oil. Third step, a mixture of 3-thiopheneylmethanamine (158 mg), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-(3-thiopheneylmethyl)-adenosine(150 mg) as a white solid: positive ESIMS m/z 364[M + H]+, 386[M + Na]+ and 402 [M + K]+; negative ESIMS m/z 362[M - H]-; 1H NMR (300MHz, DMSO-d6): the adenosine moiety delta 8.36 (2H, s, -NH, H-2), 8.22 (1H, s, H-8), 5.88 (1H, d, 6.0Hz, H-1), 5.43 (1H, d, 6.0Hz, -OH), 5.38 (1H, m, -OH), 5.17 (1H, d, 4.5Hz, -OH), 4.60 (1H, m, H-2'), 4.13 (1H, m, H-3'), 3.95 (1H, m, H-4'), 3.70-3.64 (1H, m, H-5a'), 3.58 (1H, m, H-5b'); the 3-thiopheneylmethyl moiety delta 7.43 (1H, dd, 4.8Hz, 3.0Hz, H-5"), 7.28 (1H, brs, H-2"), 7.08 (1H, dd, 4.8Hz, 0.9Hz, H-4"), 4.68 (2H, brs, H-7"); 13C NMR (75MHz, DMSO-d6): the adenosine moiety delta 154.4 (s, C-6), 152.5 (d, C-2), 148.6 (s, C-4), 140.9 (d, C-8), 119.9 (s, C-5), 88.1 (d, C-1), 86.1 (d, C-4'), 73.7 (d, C-2'), 70.8 (d, C-3'), 61.8 (t, C-5'); the 3-thiopheneylmethyl moiety delta 140.1 (s, C-3"), 127.7 (d, C-4"), 126.2 (d, C-5"), 121.8 (d, C-2"), 39.5 (t, C-6)omicron |
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