Acetamide → N-[5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-6-yl]acetamide

Participants

Role	Name	HCID	Charge
Reactant	Acetamide	HCID 178	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	6-Bromo-5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine	HCID 89579480	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-[5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-6-yl]acetamide	HCID 89579822	18.3%

Reaction Conditions

Temperature	150 °C

Reaction Steps

6-Bromo-5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (0.125 g, 0.25 mmol), acetamide (0.022 g, 0.37 mmol), cesium carbonate (0.163 g, 0.5 mmol), xantphos (0.022 g, mol %), Pd2(dba)3 (0.010 g, 5 mol %) and MeCN (2 mL) were combined and heated to 150° C. for 30 minutes. The reaction was diluted with DCM (10 mL), washed with water (10 mL), passed through a hydrophobic frit and concentrated at reduced pressure. The resulting residue was purified by basic prep HPLC to afford N-[5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-6-yl]acetamide (22 mg). LCMS [M+H]+=480.2

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09290511B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-12275e2945da450886c7df3a6417cdbb
Source note	uspto-grants-2016_03