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DOI: 10.1055/s-0031-1289888
An Efficient Copper-Catalyzed Microwave-Assisted S-Arylation towards the Synthesis of 8-Arylsulfanyl Adenines
Publication History
Publication Date:
11 November 2011 (online)
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Abstract
We report a microwave-assisted synthetic protocol for the C-S cross-coupling reaction of aryl iodides and 8-mercaptoadenine using CuI and n-Bu4NBr with NaOt-Bu in DMF. The method is rapid, simple, and cost efficient, and leads in high yields to biologically relevant aryl sulfides.
Key words
microwave - copper-catalyzed S-arylation - phase-transfer catalyst
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References and Notes
General Procedure
for the Microwave Coupling Reaction
In a conical-bottomed
Biotage microwave vial, the mixture of 8-mercaptoadenine (16 mg,
0.1 mmol), 6-iodo-2,3-benzofuran (24 mg, 0.1 mmol), CuI (3.6 mg,
0.02 mmol), NaOt-Bu (28 mg, 0.3 mmol)
and TBAB (6.4 mg, 0.02 mmol) in DMF (2 mL) was charged. The sealed
vial was irradiated in the microwave for 1.5 h at 190 ˚C.
After cooling, the reaction mixture was condensed in vacuo and purified
by flash chromatography (CH2Cl2-MeOH = 10:1)
to yield compound 8-(2,3-dihydrobenzofuran-6-ylthio)-9H-purin-6-amine (25 mg, 92%,
Table
[²]
, entry
1) as a yellow solid.
Analytical Data
¹H
NMR (500 MHz, MeOH-d
4): δ = 8.14
(s, 1 H), 7.24 (d, J = 7.6
Hz, 1 H), 7.07 (d, J = 7.3
Hz, 1 H), 6.97 (s, 1 H), 4.62 (t, J = 8.7
Hz, 2 H), 3.25 (t, J = 8.7
Hz, 2 H). ESI-MS: m/z = 285.9 [M + H]+.
ESI-HRMS: m/z [M + H]+ calcd
for C13H12N5OS: 286.0763; found:
286.0768. HPLC analyses were performed on a Waters Autopurification
system with PDA, MicroMass ZQ and ELSD detector and a reversed-phase
column (Waters X-Bridge C18, 4.6 × 150
mm, 5 µm). The mobile phase was the mixture of 5-95% MeCN-H2O with
0.1% TFA having a flow rate at 1.2 mL/min for
12 min; t
R = 7.47
min; purity, 99%; HRMS data were collected using Waters
LCT Premier XE.