cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene → [2-Chloro-5-((Z)-2-ethoxy-vinyl)-pyrimidin-4-yl]-(1-ethylpropyl)-amine

HRID 2189287Notes

Reaction equation

C([Sn](CCCC)(CCCC)/[CH:6]=[CH:7]\[O:8][CH2:9][CH3:10])CCC.Br[C:20]1[C:21]([NH:27][CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[N:22][C:23]([Cl:26])=[N:24][CH:25]=1>CC#N.[N+](CC)(CC)(CC)CC.[Cl-].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:26][C:23]1[N:22]=[C:21]([NH:27][CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:20](/[CH:6]=[CH:7]\[O:8][CH2:9][CH3:10])=[CH:25][N:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tributyl-((Z)-2-ethoxy-vinyl)-stannane (4.25 g, 8.8 mmol) in CH3CN (10 mL) is added (5-bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (2.25 g, 8 mmol), Et4NCl (1.33 g, 8 mmol) and Pd(PPh3)2Cl2 (280 mg, 0.4 mmol) at ambient temperature. The reaction mixture is purged with N2, sealed in a microwave reactor and heated at 100° C. for 20 min. After cooling to room temperature, the mixture is concentrated in vacuo and the residue is purified by flash chromatography (SiO2, EtOAc/hexane 5:95 to 40:60) to give [2-Chloro-5-((Z)-2-ethoxy-vinyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine.

Workup

customThe reaction mixture is purged with N2
customsealed in a microwave reactor
temperatureAfter cooling to room temperature
concentrationthe mixture is concentrated in vacuo
customthe residue is purified by flash chromatography (SiO2, EtOAc/hexane 5:95 to 40:60)

Sources & evidence

ORD record: ord-dfa46724380e4799be8d5bbd6eaa92f1
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324225B2

Reaction notes

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