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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1937389Generated: October 31, 2026

Pyridine → 4-(6-Chloro-2,3dihydro-indol-1-yl)-pyrido[3,4-d]pyrimidine

https://huagongshe.com/reaction/1937389

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
ReactantDichloromethaneHCID 6344—
Reactant6-Chloro-2,3-dihydro-1h-indoleHCID 258567—
Reactant4-Chloropyrido(3,4-d)pyrimidineHCID 12271634—
SolventDimethylformamideHCID 6228—
Product4-(6-Chloro-2,3dihydro-indol-1-yl)-pyrido[3,4-d]pyrimidineHCID 18473275—

Reaction Conditions

Temperature70 °C

Reaction Steps

4-Chloropyrido[3,4-d]pyrimidine (0.10 g, 0.60 mmol), 6-chloroindoline (0.10 g, 0.66 mmol) and pyridine (0.14 g, 1.81 mmol) were combined in DMF (1 mL) and heated at 70° C. for 3 hours. The reaction was cooled to room temperature and then added to methylene chloride (150 mL). The organic layer was washed with saturated sodium carbonate and water and then dried over sodium sulfate. The solvent was removed by rotary evaporation and the residue purified by column chromatography (silica gel, 9/2/1—CH2Cl2/hexanes/methanol) to give the title product as a pale yellow residue (0.048 g, 28%). MP 194-6° C.; LCMS: 283 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06395733B1
Source datasetuspto-grants-2002_05
ORD IDord-7b22fd35f8484baf9bd82b82be07c575
Source noteuspto-grants-2002_05