Triethylamine → HCID 86724250, compound

HRID 873708Notes

Reaction equation

HRID 873708 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C[Si](C)(C)[C:11]#[C:12][CH3:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N(CC)CC)C>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.[Cu]I.O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:11]#[C:12][CH3:13])[N:5]=[CH:4][N:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 803631-(Trimethylsilyl)prop-1-yneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 86724250HCID 86724250, compoundYield 40.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Under argon atmosphere, a mixture of 4,6-dichloropyrimidine (500 mg, 3.36 mmol), 1-(trimethylsilyl)-1-propyne (0.497 mL, 3.36 mmol), tetrabutylammonium fluoride (1 M in THF, 3.36 mL, 3.36 mmol), triethylamine (1.54 mL, 11.1 mmol), tetrakis(triphenylphosphine)palladium(0) (194 mg, 0.168 mmol), copper(I) iodide (192 mg, 1.01 mmol) and toluene (20 mL) was stirred for 9 hours at 60° C. The mixture was cooled down to ambient temperature, and water was added to the mixture. The mixture was extracted with CHCl3, and the organic layer was dried over MgSO4 and filtered. The filtrate was concentrated at reduced pressure, and purification of the residue with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 20%) afforded 4-chloro-6-(prop-1-yn-1-yl)pyrimidine (207 mg).

Workup

  1. temperatureThe mixture was cooled down to ambient temperature
  2. extractionThe mixture was extracted with CHCl3
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated at reduced pressure, and purification of the residue with column chromatography on silica gel (hexane-EtOAc

Sources & evidence

ORD record
ord-353044fdf04d43fe8e74d53b77c9a66d
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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