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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 390043Generated: October 29, 2026

Dimethylformamide → Ethyl 4-({3-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]phenyl}amino)-6-methyl-2-(methylthio)-5-pyrimidinecarboxylate

https://huagongshe.com/reaction/390043

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantDiisopropylethylamineHCID 81531—
ReactantEthyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 22225416—
Reactant1,1-Dimethylethyl[3-(3-aminophenyl)propyl]carbamateHCID 86654199—
ProductEthyl 4-({3-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]phenyl}amino)-6-methyl-2-(methylthio)-5-pyrimidinecarboxylateHCID 5829631429%

Reaction Conditions

Temperature75 °C

Reaction Steps

To a solution of 1,1-dimethylethyl[3-(3-aminophenyl)propyl]carbamate (390 mg, 1.558 mmol) in DMF (5 mL) were added ethyl 4-chloro-6-methyl-2-(methylthio)-5-pyrimidinecarboxylate (307 mg, 1.246 mmol) and DIEA (0.298 mL, 1.714 mmol), and the reaction mixture was stirred at 75° C. overnight. The reaction was then concentrated and the residue was purified using column chromatography (silica gel, 0% to 50% EtOAc gradient in hexane) to afford the product (210 mg, 29% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08383635B2
Source datasetuspto-grants-2013_02
ORD IDord-d5c7cda7dec54782a1da4bf527990038
Source noteuspto-grants-2013_02