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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2189306Generated: October 25, 2026

Tributyl(prop-1-yn-1-yl)stannane → 2-chloro-N-(pentan-3-yl)-5-(prop-1-ynyl)pyrimidin-4-amine

https://huagongshe.com/reaction/2189306

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributyl(prop-1-yn-1-yl)stannaneHCID 2733165—
Reactant5-bromo-2-chloro-N-(pentan-3-yl)pyrimidin-4-amineHCID 58015891—
CatalystHCID 178418397HCID 178418397—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product2-chloro-N-(pentan-3-yl)-5-(prop-1-ynyl)pyrimidin-4-amineHCID 5801595574.8%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a microwave vial is added a solution of (5-bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (0.5 g, 1.80 mmol) in anhydrous toluene (10 mL), tributyl(1-propynyl)-tin (1.1 mL, 3.6 mmol) and Pd(PPh3)4 (41.5 mg, 0.036 mmol). The reaction mixture is heated at 120° C. for 1 h by employing microwave. The reaction mixture is diluted with EtOAc, washed with NaHCO3 aqueous solution and water, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, EtOAC/hexane 1:5) gave 0.32 g of (2-chloro-5-prop-1-ynyl-pyrimidin-4-yl)-(1-ethyl-propyl)-amine

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08324225B2
Source datasetuspto-grants-2012_12
ORD IDord-e6db294ccfb348d28893616dc2af423e
Source noteuspto-grants-2012_12