Triethylamine → 6-((1H-imidazol-1-yl)methyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-(prop-2-yn-1-yl)-1H-imidazole	HCID 12591942	—
Reactant	5-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrile	HCID 17968161	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	6-((1H-imidazol-1-yl)methyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile	HCID 9943969	64%

Reaction Conditions

Temperature	80 °C

Reaction Steps

1-Prop-2-ynyl-1H-imidazole (15 mmol) is dissolved in DMF at room temperature under nitrogen atmosphere. To the solution, 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (8 mmol), triethylamine (24 mmol), copper(I) iodide (0.8 mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.4 mmol) are added successively. The mixture is heated at 80° C. under nitrogen atmosphere for 3 h. After cooling at room temperature, the mixture is diluted with H2O and AcOEt and filtered with celite. The organic layer is taken, dried over MgSO4 and evaporated in vacuo. The residue is purified by silica gel column chromatography (AcOEt:MeOH=20:1) to give 7-(2,2-dimethyl-propyl)-6-imidazol-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 64% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07452886B2
Source dataset	uspto-grants-2008_11
ORD ID	ord-b5be8e59fee24362b77d64a6ebe13980
Source note	uspto-grants-2008_11