N,N-Dimethyl-1,3-propanediamine → N-(3-(Dimethylamino)propyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethyl-1,3-propanediamine	HCID 7993	—
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	4-[4-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methylester	HCID 46182044	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(3-(Dimethylamino)propyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide	HCID 46182666	51%

Reaction Conditions

Temperature	0 °C

Reaction Steps

HATU (0.052 g, 0.138 mmol) was added into a mixture of methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (0.050 g, 0.125 mmol) and Hünig's base (22 μL, 0.125 mmol) in DMF (2.0 mL) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 hours. 3-Dimethylamino-1-propylamine (69 μL, 0.625 mmol) was added and the coolant removed. The reaction mixture was stirred at ambient temperature overnight. The product was recrystallised from DMSO to yield off-white solid (0.031 g, 51%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08486953B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-a8a25af9dbd8457b8191db1cabaac1e3
Source note	uspto-grants-2013_07