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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 734447Generated: October 29, 2026

Triphenylphosphine → (2-chloro-5-methyl-pyrimidin-4-yl)-[3-(1H-indol-5-yloxy)-propyl]-methyl-amine

https://huagongshe.com/reaction/734447

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
Reactant5-HydroxyindoleHCID 16054—
Reactant1,1'-(Azodicarbonyl)dipiperidineHCID 73042—
Reactant3-[(2-Chloro-5-methyl-4-pyrimidinyl)(methyl)amino]-1-propanolHCID 59300467—
SolventDichloromethaneHCID 6344—
SolventEthyl AcetateHCID 8857—
Product(2-chloro-5-methyl-pyrimidin-4-yl)-[3-(1H-indol-5-yloxy)-propyl]-methyl-amineHCID 5784551224.1%

Reaction Steps

To a solution of 3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]-1-propanol (0.316 g, 1.47 mmol) (prepared in similar fashion as Example 83) and 5-hydroxyindole (0.195 g, 1.47 mmol) in dichloromethane (7 mL) was added triphenylphosphine (1.15 g, 4.40 mmol) and 1,1′-(azodicarbonyl)dipiperidine (1.11 g, 4.40 mmol) under argon. The golden yellow mixture was stirred at rt for 24 h. The desired product (0.117 g, 24%) was obtained after column chromatography (50% hexanes in EtOAc). LC/MS m/z 331.3 (M+H)+, RT 2.76 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07592361B2
Source datasetuspto-grants-2009_09
ORD IDord-e4a30b16a45a4831b686ede0ae92eb62
Source noteuspto-grants-2009_09