5-Bromo-6-iodobenzo[d][1,3]dioxole → 8-(6-Bromo-benzo[1,3]dioxol-5-ylsulfanyl)adenine

Participants

Role	Name	HCID	Charge
Reactant	5-Bromo-6-iodobenzo[d][1,3]dioxole	HCID 3549864	—
Reactant	2,9-Dimethyl-1,10-phenanthroline hydrate	HCID 16211234	—
Reactant	sodium 2-methylpropan-2-olate	HCID 178418730	—
Reactant	HCID 178508691	HCID 178508691	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	8-(6-Bromo-benzo[1,3]dioxol-5-ylsulfanyl)adenine	HCID 11474022	97.9%

Reaction Conditions

Temperature	110 °C

Reaction Steps

8-Mercaptoadenine (602 mg, 3.6 mmol), neocuproine hydrate (81 mg, 0.36 mmol), CuI (69 mg, 0.36 mmol), NaO-t-Bu (692 mg, 7.2 mmol), 5-bromo-6-iodo˜benzo[1,3]dioxole (3.53 g, 10.8 mmol) and anhydrous DMF (24 mL) were charged in a nitrogen box. The vessel was sealed with Teflon tape, placed in an oil bath (110° C.) and magnetically stirred for 24 h. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel (EtOAc:CH2C12:MeOH at 2:2:1) to provide the product (1.29 g, 97%). 1H NMR (400 MHz, acetone-d6) 8.07 (s, 1H), 7.28 (s, 1H), 7.15 (s, 1H), 7.08 (bs, 2H), 6.13 (s, 2H); MS m/z 366.0 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403828B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-dd763d55aa3b4ccfbb3391a70a30cd40
Source note	uspto-grants-2016_08