Lithium hydroxide, monohydrate → 4-(5-Chloro-2-cyclopropylaminopyrimidin-4-yl)benzoic acid

Participants

Role	Name	HCID	Charge
Reactant	Lithium hydroxide, monohydrate	HCID 168937	—
Reactant	Methyl 4-(5-chloro-2-(cyclopropylamino)pyrimidin-4-yl)benzoate	HCID 69422210	—
Solvent	Hydrochloric Acid	HCID 313	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-(5-Chloro-2-cyclopropylaminopyrimidin-4-yl)benzoic acid	HCID 69422183	90%

Reaction Conditions

Temperature	50 °C

Reaction Steps

4-(5-Chloro-2-cyclopropylaminopyrimidin-4-yl)-benzoic acid methyl ester (90 mg, 0.30 mmol) was dissolved in THF and 50 mg (1.2 mmol) of lithium hydroxide monohydrate dissolved in water was added. The reaction mixture was heated to 50° C. for 5 hours, cooled to room temperature, diluted with 1N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to afford 4-(5-chloro-2-cyclopropylaminopyrimidin-4-yl)-benzoic acid as a yellow solid, 78 mg, 0.27 mmol, 90% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07304071B2
Source dataset	uspto-grants-2007_12
ORD ID	ord-4a2d16a19aa74ccda9d7fbb4ac6d9b99
Source note	uspto-grants-2007_12