Isopropylamine → 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(1-methylethyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Isopropylamine	HCID 6363	—
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-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid	HCID 11950622	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(1-methylethyl)benzamide	HCID 11950821	97,322.797%

Reaction Steps

To the solution of 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid (150 mg, 0.34 mmol) in CH2Cl2 (10 mL) were added isopropylamine (0.087 mL, 1.02 mmol), HATU (135 mg, 0.355 mmol) and diisopropyl ethyl amine (0.2 mL, 1.15 mmol). The reaction mixture was stirred over night. The reaction mixture was diluted with CH2Cl2 (50 mL) and water (50 mL) and shaked. The layers were separated and the organic layer was washed with brine (75 mL), dried over Na2SO4, filtered and concentrated. Flash chromatography then provided the title compound as a white solid 160 g (97%). LC-MS m/z 484 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07674789B2
Source dataset	uspto-grants-2010_03
ORD ID	ord-8579dc34b77a4f6fa0393c9eaa8a9d36
Source note	uspto-grants-2010_03