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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1155068Generated: October 30, 2026

Thionyl Chloride → 4-Amino-5-(4-chloro-2-methoxy-benzoylamino)-pyrimidine

https://huagongshe.com/reaction/1155068

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant4-Chloro-o-anisic acidHCID 93682—
ReactantPyrimidine-4,5-diamine dihydrochlorideHCID 20562693—
Reactant4-Chloro-2-methoxybenzoyl chlorideHCID 22142450—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventPyridineHCID 1049—
Product4-Amino-5-(4-chloro-2-methoxy-benzoylamino)-pyrimidineHCID 20562711—

Reaction Steps

The 4-chloro-2-methoxy-benzoyl chloride prepared from 5.6 g of 4-chloro-2-methoxy-benzoic acid and 100 ml of thionyl chloride was dissolved as crude product in 100 ml of pyridine and mixed successively with 5 g of 4,5-diaminopyrimidine dihydrochloride and 1 g of 4-dimethylamino pyridine. After stirring for at first 2 hours at room termperature and then for 1.5 hours at 100° C., the reaction mixture was evaporated to dryness, mixed with water, and neutralized with sodium bicarbonate. The precipitate obtained was used in the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04299834
Source datasetuspto-grants-1981_11
ORD IDord-f1c433141f824c62825e2d1e77af32cb
Source noteuspto-grants-1981_11