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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2200884Generated: November 1, 2026

Water → 2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid

https://huagongshe.com/reaction/2200884

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTriethylamineHCID 8471—
Reactant3-Azabicyclo[3.1.0]hexane hydrochlorideHCID 22335289—
ReactantAvanafil Impurity 37HCID 118157672—
SolventTetrahydrofuranHCID 8028—
Product2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acidHCID 117622545—

Reaction Steps

In THF (15 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl) pyrimidine-5-carboxylic acid (196 mg, 0.55 mmol) and 3-azabicyclo[3.1.0]hexane hydrochloride salt (79 mg, 0.66 mmol). The solution was cooled in an ice bath, and triethylamine (167 mg, 1.65 mmol) was added dropwisely. The reaction was allowed to warm to ambient temperature for 5 h, followed by addition of water and extracted with DCM. The organic phase was dried and concentrated to give a solid which was used in the subsequent procedure without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359371B2
Source datasetuspto-grants-2016_06
ORD IDord-ec6d8a4ba0e94617b6fa3d41830c869b
Source noteuspto-grants-2016_06