Reaktion #720960

Reaktionsgleichung

compound 3

4-Amino-7-(β-D-ribofuranosyl)-5-[(trimethylsilyl)ethynyl]-7H-pyrrolo[2,3-d]pyrimidine

K2CO3

→

title compound 2o

Ausbeute 96.2%

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

Ausbeute 96.2%

Lösungsmittel

MeOH

Reaktionsbedingungen

Vorschrift

A mixture of the compound 3 from Step 1 (686 mg, 1.89 mmol) and K2CO3 (130 mg, 0.94 mmol) in MeOH (15 ml) was stirred at RT for 1 h, followed by the co-evaporation with silica. Column chromatography on silica (5% MeOH in CHCl3) provided title compound 2o as white crystalline solid (528 mg, 96%). Compound was recrystallized from MeOH/water as long ochry needles. Mp 215-217° C. [α]D −88.3 (c 0.524, DMSO). 1H NMR (500.0 MHz, DMSO-d6): 3.53 (ddd, 1H, Jgem=12.0, J5′b,OH=6.2, J5′b,4′=3.8, H-5′b); 3.63 (dd, 1H, Jgem=12.0, J5′a,OH=5.0, J5′a,4′=3.8, H-5′a); 3.89 (td, 1H, J4′,5′=3.8, J4′,3′=3.2, H-4′); 4.07 (ddd, 1H, J3′,2′=5.0, J3,OH=4.8, J3′,4′=3.2, H-3′); 4.29 (s, 1H, HC≡C—); 4.37 (ddd, 1H, J2′,OH=6.3, J2′,1′6.1, J2′,3′5.0, H-2′); 5.16 (d, 1H, JOH,3′=4.8, OH-3′); 5.23 (dd, 1H, JOH,5′=6.2, J2′,3′5.0, OH-5′); 5.38 (d, 1H, JOH,2′=6.3, OH-5′); 6.01 (d, 1H, J1′,2′=6.1, H-1′); 6.70 (bs, 2H, NH2); 7.83 (s, 1H, H-6); 8.12 (s, 1H, H-2). 13C NMR (125.7 MHz, DMSO-d6): δ1.73 (CH2-5′); 70.74 (CH-3′); 74.21 (CH-2′); 77.52 (—CCH); 83.37 (—CCH); 85.51 (CH-4′); 87.42 (CH-1′); 94.17 (C-5); 102.65 (C-4a); 127.74 (CH-6); 149.73 (C-7a); 153.04 (CH-2); 157.78 (C-4). MS (ESI) m/z 291 (M+H), 313 (M+Na). HRMS (ESI) for C13H15N4O4 [M+H] calcd: 291.1088. found: 291.1088. Anal. Calcd for C13H14N4O4: C, 53.79; H, 4.86; N, 18.91. Found: C, 53.34; H, 4.95; N, 18.97.

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