Cesium carbonate → Methyl 4-methyl-3-(4-phenylpyrimidin-2-ylamino)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Amino-4-phenylpyrimidine	HCID 598777	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Methyl 3-bromo-4-methylbenzoate	HCID 7015747	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	Methyl 4-methyl-3-(4-phenylpyrimidin-2-ylamino)benzoate	HCID 68466271	52.2%

Reaction Conditions

Temperature	130 °C

Reaction Steps

A mixture of 4-phenylpyrimidin-2-amine (100 mg, 0.58 mmol) and methyl 3-bromo-4-methylbenzoate (111 mg, 0.48 mmol), Cs2CO3 (221 mg, 0.68 mmol), Pd2(dba)3 (22 mg, 0.024 mmol) and Xantphos (22 mg, 0.039 mmol) in a microwave reaction vessel was suspended in 5 mL of toluene. The reaction mixture was heated in a microwave at 130° C. for 30 min, and then at 180° C. for 30 min. After cooling, the mixture was purified by ISCO system to give 80 mg of product (yield: 43%). MS (ESI+) m/z 320.1 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08367686B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-f292fd24b2054d5c854f4ca62260dc6d
Source note	uspto-grants-2013_02