1: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.5 h / -10 °C 2: ethanol / 5 h / 100 °C View Scheme

1: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.5 h / -10 °C 2: methanol / 3 h / |Reflux View Scheme

1: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.5 h / -10 °C 2: ethanol / 4 h / 20 °C View Scheme

ammonia in methanol T=120 - 130°C;

1: water; 1,4-dioxane / 8 h / 120 °C 2: sodium carbonate; triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt; palladium diacetate / water; acetonitrile / 1 h / 100 °C / |Inert atmosphere View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '3607348', constants.ctx, '0')">4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1306669', constants.ctx, '0')">N,0-bis(trimethylsilyl)acetamide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />T=20&deg;C;&nbsp;0.333333&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '100243', constants.ctx, '0')">1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1868911', constants.ctx, '0')">trimethylsilyl trifluoromethanesulfonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />T=20 - 80&deg;C;&nbsp;2.5&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: potassium hydroxide; iodine / DMFA / 0.5 h / 20 &deg;C<br />2.1: (E)-trimethylsilyl-N-(trimethylsilyl)acetimidate / acetonitrile / 0.25 h / 20 &deg;C<br />2.2: 1.75 h / 20 - 80 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: acetonitrile / 0.17 h / 20 &deg;C<br />2: 171 mg / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1 h / 80 &deg;C<br /> <br /> &nbsp;