Hydrochloric Acid → N-(3-dimethylaminomethyl-phenyl)-N'-methyl-pyrimidine-4,6-diamine

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	3-amino-N,N-dimethylbenzylamine	HCID 99294	—
Reactant	3-(2,6-Dichloro-3-methoxy-phenyl)-1-methyl-1-(6-[4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl)-urea	HCID 56594745	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(3-dimethylaminomethyl-phenyl)-N'-methyl-pyrimidine-4,6-diamine	HCID 66669947	59.8%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A mixture of (6-chloro-pyrimidin-4-yl)-methyl-amine (Example 1) (750 mg, 5.2 mmol), 3-dimethylaminomethyl-phenylamine (787 mg, 5.2 mmol) and 4N HCl in dioxane (15 ml) is heated in a sealed tube to 150° C. for 5 h. The reaction mixture is concentrated, diluted with DCM and a saturated aqueous solution of sodium bicarbonate. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) affords 800 mg of the title compound as a white solid: ESI-MS: 258.1 [MH]+; tR=1.00 min (purity: 100%, gradient J); TLC: Rf=0.14 (DCM/MeOH+1% NH3aq, 9:1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08552002B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-a19e0b18adb94208bef9924b496ac1fa
Source note	uspto-grants-2013_10