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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 500761Generated: October 31, 2026

4-(2-Fluoro-4-nitrophenoxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine → 4-(5-Methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3-fluorobenzenamine

https://huagongshe.com/reaction/500761

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-(2-Fluoro-4-nitrophenoxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidineHCID 59424577—
CatalystIronHCID 23925—
SolventAcetic AcidHCID 176—
SolventDichloromethaneHCID 6344—
Product4-(5-Methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3-fluorobenzenamineHCID 5942458853.1%

Reaction Steps

To a solution of 4-(2-fluoro-4-nitrophenoxy)-5-methyl-5H-pyrrolo[3,2-d] pyrimidine (29) (253.6 mg, 0.879 mmol) in AcOH (3 mL) at 90° C. was added iron powder (245 mg, 4.4 mmol). The mixture was stirred vigorously for 10 min and filtered. The filtrate was concentrated under reduced pressure to produce a solid, which was dissolved in DCM. The resultant solution was washed with cold NaHCO3 solution and water, dried over Na2SO4 and concentrated to provide a residue which was purified by column chromatography (eluent MeOH—CH2Cl2 1:20) to afford the title compound 30 as a brown solid (120.6 mg, 53% yield). LRMS (M+1) 240.1 (100%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07772247B2
Source datasetuspto-grants-2010_08
ORD IDord-123691c414614923b6f53bbb0a759a74
Source noteuspto-grants-2010_08