1-Chloro-2,4-Dinitrobenzene → 3-(2-tert-Butoxyethoxy)-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Participants

Role	Name	HCID	Charge
Reactant	1-Chloro-2,4-Dinitrobenzene	HCID 6	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	O-(2-tert-butoxyethyl)hydroxylamine	HCID 46856370	—
Reactant	5-((2-Fluoro-4-iodophenyl)amino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione	HCID 135741732	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	3-(2-tert-Butoxyethoxy)-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione	HCID 58191937	12%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Compound 5F (250 mg, 0.61 mmol), potassium carbonate (209 mg, 1.51 mmol) and 1-chloro-2,4-dinitrobenzene (307 mg, 1.51 mmol) were stirred in DMA at 80° C. for 1.5 h. O-(2-tert-Butoxy-ethyl)-hydroxylamine was added at r.t and the reaction was stirred for 1 h at 80° C. Purification by prep-HPLC gave 43 mg (12%) of the title compound as an off-white solid. MS (ES) [m+H] calc'd for C20H22FIN4O4, 529; found 529.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08030317B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-5bfb155e7916496bb1cc787e050a9e44
Source note	uspto-grants-2011_10