(4-prop-2-ynylcyclohexyl)methyl Acetate → [4-(3-{9[(4s,5s,2r,3r)-5-(n-Ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-6-aminopurin-2-yl}prop-2-ynyl)cyclohexyl]methyl acetate

Participants

Role	Name	HCID	Charge
Reactant	(4-prop-2-ynylcyclohexyl)methyl Acetate	HCID 10726483	—
Reactant	(2s,3s,4r,5r)-5-(6-Amino-2-Iodo-9h-Purin-9-Yl)-N-Ethyl-3,4-Dihydroxytetrahydrofuran-2-Carboxamide	HCID 11697766	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[4-(3-{9[(4s,5s,2r,3r)-5-(n-Ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-6-aminopurin-2-yl}prop-2-ynyl)cyclohexyl]methyl acetate	HCID 9892191	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a degassed solution of 125 mg (0.29 mmol) of [(2S,3S,4R,5R)-5-(6amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-N-ethylcarboxamide (6.9), 150 mg (0.77 mmol) (5.6), and 1.0 mg CuI in 1.3 mL of TEA and 4 mL DMF was added 25 mg of Pd(PPh3)4. The solution was stirred for 72 h at 60° C. after which time the solution was filtered through celite and chromatographed on silica gel with MeOH-CHCl3 (5:95) to give JMR193 (10%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06322771B1
Source dataset	uspto-grants-2001_11
ORD ID	ord-d4c38c6ea9b7459a93f4f0480a579d07
Source note	uspto-grants-2001_11