Sodium Bicarbonate → HCID 46701977, compound

https://huagongshe.com/reaction/2090445

Participants

Role	Name	HCID	Charge
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	1-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester	HCID 11230491	—
Reactant	4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine	HCID 59402317	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Methanol	HCID 887	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 46701977	HCID 46701977	50.8%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (10 mg, 0.02 mmol; Peak 1, Example 49, Step 7), 1-(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (9.1 mg, 0.036 mmol), tetrakis(triphenylphosphine)palladium(0) (1.4 mg, 0.0012 mmol), and sodium bicarbonate (6.0 mg, 0.072 mmol) in 1,4-dioxane (0.2 mL) and water (0.1 mL) was stirred at 90° C. for 2 h. After cooling, it was diluted with methanol, and purified with RP-HPLC (pH=10). to afford the desired product (4.7 mg). LCMS (M+H)+: m/z=463.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08436008B2
Source dataset	uspto-grants-2013_05
ORD ID	ord-edffcaf5bd3b4e51a4afbfb6c62bb091
Source note	uspto-grants-2013_05