ChemicalBook CAS DataBase List 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE

2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE synthesis

7synthesis methods

Product Name:2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE
CAS Number:141018-29-3
Molecular formula:C12H15IN6O4
Molecular Weight:434.19

162936-24-5 Synthesis

2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDINEADENOSINE

162936-24-5
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$62.50/5mg

141018-29-3
19 suppliers
$60.00/2mg

Yield:141018-29-3 99%

Reaction Conditions:

with trifluoroacetic acid in water at 20; for 1.08333 h;

Steps:

A.A4; 4 SCHEME A; step A4; Example 4: Synthesis of [(2S,3S,4R,5R)-5-(6-amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolan-2yl]-N-ethylcarboxamide (Compound 5)

To a stirred solution of 10% aqueous trifluoroacetic acid (1100 mL) is added Compound 4 (80 g, 168 mmol) over 5 minutes with stirring. The solution was stirred for 1 hour at room temperature, and then concentrated under reduced pressure. The resulting brown oil was triturated with methyl tert-butyl ether (MTBE) to afford a solid which was filtered, rinsed with MTBE, and dried under vacuum to yield Compound 5 (72.7 g, 99%) as a white POWDER. 1H-NMR (600 MHz, DMSO-D6) : 1.05 (t, 3H), 3.24 (M, 2H), 4.17 (dd, 1H), 4.31 (d, 1H), 4.58 (dd, 1H), 5.91 (d, 1H), 7.74 (bs, 2H), 8.10 (t, 1H), 8.38 (s, 1H) ; 13C-NMR (150 MHz, DMSO-d6): 14.78, 26.77, 33. 47, 72.65, 72.94, 84.20, 119.16, 120. 91,149. 84, 155.90, 169.00 ; LRMS (ES): m/z = 435.1 (M+H, 100%)

References:

WO2004/104017,2004,A2 Location in patent:Page 18; 33