Diisopropylethylamine → (4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanone

Participants

Role	Name	HCID	Charge
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	3-(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acid	HCID 57600107	—
Reactant	(2-chloro-5,5-dioxo-6,7-dihydro-5H-5lambda6-thieno[3,2-d]pyrimidin-4-yl)propylamine	HCID 86616274	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	(4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanone	HCID 86616277	33%

Reaction Steps

0.600 g (1.95 mmol) of 3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acid (I), 0.741 g (1.95 mmol) of O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), and 0.680 mL (3.90 mmol) of is diisopropylethylamine are placed in 10 mL of dimethylsulfoxide, then stirred for 0.5 hours at ambient temperature. 0.220 mL (1.95 mmol) of methylpiperazine (II) is added, then the mixture is stirred for 3 hours at ambient temperature. Then the reaction mixture is concentrated by evaporation and the residue is combined with water. Any precipitate formed is suction filtered and dried. The crude product is purified by chromatography through a 50 g silica cartridge with ethyl acetate/methanol 8:2. 0.250 g of product III (33%) is obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08354531B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-576ddd9f4f8845ffb8b3373a93bf99fd
Source note	uspto-grants-2013_01