2-O-Methylcytosine → N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine

Participants

Role	Name	HCID	Charge
Reactant	2-O-Methylcytosine	HCID 160679	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine	HCID 59823198	—
Catalyst	palladium(II) acetate	HCID 167845	—
Product	N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	HCID 68650127	48%

Reaction Conditions

Temperature	200 °C

Reaction Steps

To a solution of 2-methoxypyrimidin-4-amine (0.1 mmol) and N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine (0.1 mmol) in 3 ml dioxide, CsCO3 (0.2 mmol), Pd(OAc)2 (10 mmol %) and Xantphos (10 mmol %) were added. The mixture was stirred under microwave irradiation at 200° C. for 40 mins. After cooling the solution was filtered and the filtrate was concentrated in vacuo, the residue was purified by column chromatography (C-18) to give N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine (yield 48%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08901143B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-fb27853d38284dce9cd5424dd53c1920
Source note	uspto-grants-2014_12