Tributyl(2-phenylethynyl)stannane → HCID 178517722, compound

HRID 2059847Notes

Reaction equation

HRID 2059847 reaction equation
C([Sn](CCCC)(CCCC)[C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)CCC.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(O[C:41]1[CH:46]=[CH:45][N:44](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:43](=[O:66])[N:42]=1)(=O)=O)(C)C>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]1([C:7]#[C:6][C:41]2[CH:46]=[CH:45][NH:44][C:43](=[O:66])[N:42]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 630640Tributyl(2-phenylethynyl)stannaneHCID 585798862-Oxo-1-trityl-1,2-dihydropyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate

Product 1

HCID 178517722HCID 178517722, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Tributyl(phenylethynyl)stannane (315 mg, 0.8 mmol) was added to a stirred solution of 2-oxo-1-trityl-1,2-dihydropyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate Part A (200 mg, 0.3 mmol), copper (I) iodide (18.4 mg, 0.1 mmol) and palladium tetrakis (55.8 mg, 0.05 mmol) in 5 mL DMF under nitrogen. The reaction mixture was heated at 55° C. for 16 h, concentrated and subjected to flash chromatography (silica gel/methylene chloride to 15% MeOH-methylene chloride gradient to afford 4-(phenylethynyl)pyrimidin-2(1H)-one 4B (66 mg) as a brownish solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-029522b1c85d447bbff0fdaa0fb8b00e
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

Loading…