1,2-Diaminocyclohexane, trans- → 2-Chloro-7-(4-methanesulfonyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

https://huagongshe.com/reaction/1966393

Participants

Role	Name	HCID	Charge
Reactant	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1,1'-[Sulfonylbis(methylene)]bis(4-bromobenzene)	HCID 267419	—
Reactant	2-Chloro-7H-pyrrolo[2,3-d]pyrimidine	HCID 5706774	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Chloro-7-(4-methanesulfonyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine	HCID 45257558	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

In a seal tube, 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (600 mg, 3.56 mmol), 4-bromophenylmethylsulfone (700 mg, 4.10 mmol), CuI (239 mg, 1.23 mmol), and K3PO4 (2.67 g, 12.3 mmol) are suspended in 1,4-dioxane (30 mL). Then, trans-1,2-diaminocyclohexane (149 μL, 1.23 mmol) is added at rt. The reaction vial is flushed with Ar and the mixture is heated to 110° C. for 3 h. After cooling to rt, the reaction mixture is concentrated under reduce pressure. The residue is suspended in EtOAc and washed with saturated aqueous NaCl solution (3×). The organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure. The solid residue is triturated with small amounts of EtOAc to yield the title compound as a brown solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08420657B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-4913325d500641f596b4bdf634a9a43a
Source note	uspto-grants-2013_04