Tributylvinyltin → HCID 68726425, compound

HRID 2093619Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8](Cl)=[N:9][CH:10]=1)=[O:4].[CH2:12]([Sn](CCCC)(CCCC)C=C)[CH2:13]CC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([CH:12]=[CH2:13])=[N:9][CH:10]=1)=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of methyl-2-chloropyrimidine-5-carboxylate (2.084 g, 12.08 mmol) and tributyl(vinyl)tin (3.635 g, 11.46 mmol) in toluene (15 ml) was added triphenylphosphine (94.9 mg, 0.362 mmol) followed by tetrakis(triphenylphosphine) palladium(0) (418.5 mg, 0.362 mmol). The mixture was stirred at 110° C. for 10 h under anhydrous argon. After evaporation of solvent, the residue was purified by flash chromatography (hexanes-ethyl acetate=4:1, then 1:1) to give the title compound (0.842 g) as a white solid. Mass spectrum (ESI) 166.2 (M+1). 1H NMR (500 MHz, CDCl3) δ 9.26 (s, 2H), 6.95-7.01 (m, 1H), 6.82 (dd, 1H, J=1.4, 17.2 Hz), 5.92 (dd, 1H, J=1.4, 10.5 Hz), 4.01 (s, 3H).

Workup

customAfter evaporation of solvent
customthe residue was purified by flash chromatography (hexanes-ethyl acetate=4:1

Sources & evidence

ORD record: ord-44738ca3b9ca4b12bdae11359cdbc92c
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445480B2

Reaction notes

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