Reaktion #720961

Reaktionsgleichung

2o

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

{ compound

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

TMSN3

DMF

→

title compound 2p

Ausbeute 24.0%

4-Amino-7-(β-D-ribofuranosyl)-5-(1H-1,2,3-triazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

Ausbeute 24.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn argon purged
2. 2
   SonstigeVolatiles were evaporated under reduced pressure
3. 3
   Filtrationfiltered through celite

Vorschrift

An argon purged mixture of 7-ethynyltubericidine 2o {compound from example 15} (200 mg, 0.69 mmol), CuI (6.5 mg, 0.03 mmol) and TMSN3 (150 μl, 1.15 mmol) in MeOH (0.2 ml)/DMF (1.8 ml) was stirred 100° C. for 24 h. Volatiles were evaporated under reduced pressure, the residue was twice co-evaporated with MeOH and rest was suspended in MeOH and filtered through celite. Filtrate was co-evaporated with silica and column chromatography on silica afforded title compound 2p as yellowish solid (55 mg, 24%). Compound was recrystallized from water. Mp 286-288° C. [α]D −70 (c 0.217, DMSO). 1H NMR (499.8 MHz, DMSO-d6, t=60° C.): 3.58 (dd, 1H, Jgem=11.9, J5′b,4′=4.2, H-5′b); 3.68 (dd, 1H, Jgem 11.9, J5′a,4′=3.9, H-5′a); 3.93 (ddd, 1H, J4′,5′=4.2, 3.9, J4′,3′=3.6, H-4′); 4.15 (dd, 1H, J3′,2′=5.3, J3′,4′=3.6, H-3′); 4.45 (dd, 1H, J2′,1′=6.0, J2′,3′=5.3, H-2′); 4.93, 5.04 and 5.17 (3×bs, 3×1H, OH-2′,3′,5′); 6.08 (d, 1H, J1′,2′=6.0, H-1′); 7.85 (bs, 2H, NH2); 7.91 (s, 1H, H-6); 8.09 (s, 1H, H-2); 8.23 (s, 1H, H-5-triazole). 13C NMR (125.7 MHz, DMSO-d6, t=60° C.): 61.83 (CH2-5′); 70.54 (CH-3′); 73.72 (CH-2′); 85.15 (CH-4′); 87.41 (CH-1′); 100.16 (C-4a); 105.83 (C-5); 120.80 (CH-6); 126.16 (CH-5-triazole); 141.51 (C-4-triazole); 151.04 (C-7a); 152.35 (CH-2); 158.04 (C-4). MS (ESI) m/z 334 (M+H), 356 (M+Na). HRMS (ESI) for C13H16N7O4 [M+H] calcd: 334.1258. found: 334.1258. Anal. Calcd for C13H15N7O4: C, 46.85; H, 4.54; N, 29.42. Found: C, 47.12; H, 4.82; N, 27.96.

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