Cesium carbonate → Methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Methyl isonipecotate	HCID 424914	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine	HCID 71534185	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylate	HCID 68379345	56.3%

Reaction Steps

To a mixture of 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 0.62 mmol), methyl piperidine-4-carboxylate (177 mg, 1.24 mmol), Cs2CO3 (404 mg, 1.24 mmol), X-Phos (20 mg, 0.042 mmol), Pd(dba)2 (20 mg, 0.035 mmol) in 30 mL of dioxane were stirred at 100° for 18 hours under N2 atmosphere. The excess of dioxane was removed under reduced pressure and the residue was purified by silica gel chromatography (eluting with a mixture of petroleum ether and ethyl acetate=3:1) to give methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylate (150 mg, 56%) as a yellow solid. LC-MS: 430 [M+H]+, tR=1.63 min

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08921383B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-416366d7038f4d3aaa93eb19d5453b36
Source note	uspto-grants-2014_12