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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 16450Generated: October 25, 2026

Hydrochloric Acid → Methyl 2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}-pyrimidine-4-carboxylate

https://huagongshe.com/reaction/16450

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantMethyl 2-amino-6-chloropyrimidine-4-carboxylateHCID 239687—
ReactantSodium BicarbonateHCID 516892—
Reactant4-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroanilineHCID 16037965—
SolventEthanolHCID 702—
SolventWaterHCID 962—
ProductMethyl 2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}-pyrimidine-4-carboxylateHCID 17979310—

Reaction Conditions

Temperature100 °C

Reaction Steps

0.209 g (1.12 mmol) of methyl 2-amino-6-chloropyrimidine-4-carboxylate (prepared according to G. Doyle Daves, Fred Baiocchi, Roland K. Robins, and C. C. Cheng, J. Org. Chem., 26 (1961), 2755-2763) and 0.4 g (1.12 mmol) of [3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine (example XIX) are suspended in 5 ml of water and 5 ml of ethanol. 0.11 ml (1.34 mmol) of 37% strength hydrochloric acid is added. The mixture is stirred at 100° C. for 18 hours. After cooling, the mixture is neutralized using an aqueous saturated sodium bicarbonate solution. The resulting precipitate is filtered off with suction and dried. This gives 0.46 g of product (68% of theory).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07737153B2
Source datasetuspto-grants-2010_06
ORD IDord-d374a93459db40659be73da1475c8cba
Source noteuspto-grants-2010_06