1,1'-Carbonyldiimidazole → 2-(tetrahydro-pyran-4-ylamino)-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid [4-(4-chloro-3-fluoro-phenoxy)-1-methyl-pyrrolidin-3-yl]-amide

Participants

Role	Name	HCID	Charge
Reactant	1,1'-Carbonyldiimidazole	HCID 68263	—
Reactant	N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine	HCID 71743546	—
Reactant	trans-(+/-)-4-(4-Chloro-3-fluorophenoxy)-1-methylpyrrolidin-3-amine	HCID 86705587	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-(tetrahydro-pyran-4-ylamino)-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid [4-(4-chloro-3-fluoro-phenoxy)-1-methyl-pyrrolidin-3-yl]-amide	HCID 60198966	—

Reaction Steps

To a solution of 428 (0.085 g, 0.347 mmol) and DCM (15 mL) was added TEA (1 mL) and CDI (0.149 g, 0.919 mmol). The mixture was stirred at RT for 1 h and then 28 (0.081 g, 0.35 mmol) was added. The reaction was stirred at RT for 2 h. The solvent was removed in vacuo and the residue was purified by preparative reverse HPLC to afford 31 mg (28%) of I-151 as a white solid: LC-MS (ESI) m/z 505 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133187B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-c8109e521ca540198329c4d439437e6f
Source note	uspto-grants-2015_09