Potassium Phosphate, Tribasic → 6-(1,4-Diazabicyclo[3.2.2]nonan-4-yl)-3-methylthieno[2,3-d]pyrimidin-4(3H)-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	L-Proline	HCID 145742	—
Reactant	1,4-Diazabicyclo(3.2.2)nonane	HCID 398407	—
Reactant	6-bromo-3-methylthieno[2,3-d]pyrimidin-4(3H)-one	HCID 68160197	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Acetic Acid	HCID 176	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Methanol	HCID 887	—
Product	6-(1,4-Diazabicyclo[3.2.2]nonan-4-yl)-3-methylthieno[2,3-d]pyrimidin-4(3H)-one	HCID 68160097	2.1%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of 6-bromo-3-methylthieno[2,3-d]pyrimidin-4(3H)-one (70 mg, 0.28 mmol), copper(I) iodide (13.6 mg, 0.071 mmol), L-proline (16.4 mg, 0.143 mmol), 1,4-diazabicyclo[3.2.2]nonane (54.1 mg, 0.428 mmol) and potassium phosphate (132 mg, 0.571 mmol) in DMSO (1 mL) was heated at 90° C. in a sealed vessel for 3 days. The reaction was acidified with acetic acid, diluted with methanol and purified on a scx cartridge (1 g), further purified by acid prep HPLC, passed through a scx cartridge (500 mg) and evaporated to dryness to afford 6-(1,4-Diazabicyclo[3.2.2]nonan-4-yl)-3-methylthieno[2,3-d]pyrimidin-4(3H)-one (1.8 mg, 0.006 mmol).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841289B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-577e0f506d014acb9049cec4c76da0ea
Source note	uspto-grants-2014_09