Reaktion #44345

Reaktionsgleichung

1-Ethynyl-3-methyl-cyclohexanol

2-iodo-NECA

→

5-[6-Amino-2-(1-hydroxy-3-methyl-cyclohexylethynyl)-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-carboxylic acid ethylamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigegave JR3179 (15.0 mg, 59%) as a white solid
2. 2
   Sonstigeafter purification by a silica plug and RP-HPLC

Vorschrift

The reaction of 1-Ethynyl-3-methyl-cyclohexanol (JR3149B) (100 mg, 0.72 mmol) with 2-iodo-NECA (25 mg, 0.06 mmol) under the general coupling conditions gave JR3179 (15.0 mg, 59%) as a white solid after purification by a silica plug and RP-HPLC. 1H NMR (CD3OD-d4) δ 8.49 (s, 1 H), 6.06 (d, J=6.9 Hz, 1 H), 4.75 (dd, J=6.4 Hz, J=4.9 Hz, 1 H), 4.46 (d, J=1.9 Hz, 1 H), 4.34 (dd, J=4.9 Hz, J=2.1 Hz, 1 H), 3.42 (m, 2 H), 2.09 (d, J=12.3 Hz, 2 H), 1.73 (m, 4 H), 1.46 (m, 1 H), 1.23 (m, 1 H), 1.16 9 (t, J=7.1 Hz, 3 H), 0.95 (d, J=6.2 Hz, 3 H), 0.89 (m, 1 H). 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 445.3 (MH+, 100), 427.4 (40), 254.4 (4).

Quelle