N,N-Dimethylethylenediamine → N-(2-(dimethylamino)ethyl)-5-methyl-4-(2-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-ylamino)thieno[2,3-d]pyrimidine-6-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylethylenediamine	HCID 66053	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	5-methyl-4-(2-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-ylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid	HCID 58413102	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(2-(dimethylamino)ethyl)-5-methyl-4-(2-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-ylamino)thieno[2,3-d]pyrimidine-6-carboxamide	HCID 46182129	22.8%

Reaction Conditions

Temperature	0 °C

Reaction Steps

HATU (0.105 g, 0.28 mmol) was added into a mixture of 5-methyl-4-(2-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-ylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid (0.097 g, 0.25 mmol) and Hünig's base (44 μL, 0.25 mmol) in DMF (2.0 mL) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 hours. N,N-Dimethylethylenediamine (137 μL, 1.25 mmol) was added and the coolant removed. The reaction mixture was stirred at ambient temperature overnight. The solvent was concentrated in vacuo and the product purified by reverse phase preparative HPLC to yield off-white solid (0.026 g, 22%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08486953B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-e35f1805439b4832a00a2320b49fc3bc
Source note	uspto-grants-2013_07