Triethylamine → HCID 86626702, compound

HRID 1926134Notes

Reaction equation

HRID 1926134 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:20][C:21]2[C:26]([NH:27][CH3:28])=[C:25](I)[N:24]=[CH:23][N:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1.[CH2:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C:31]#[CH:32].C(N(CC)CC)C>C(#N)C.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.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]([NH:20][C:21]2[C:26]3[N:27]([CH3:28])[C:31]([CH2:30][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:32][C:25]=3[N:24]=[CH:23][N:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 86626703HCID 86626703, compound

Product 1

HCID 86626702HCID 86626702, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of N4-{3-chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}-6-iodo-N5-methylpyrimidine-4,5-diamine (1.53 g), tert-butyl prop-2-ynylcarbamate (0.67 g) and triethylamine (1.19 mL) in acetonitrile (28 mL) were added bis(triphenylphosphine)palladium(II) dichloride (100 mg) and copper(I) iodide (32.5 mg) at room temperature. Under an argon atmosphere, the mixture was stirred at room temperature for 4.5 hrs, heated at 50° C., and the mixture was stirred for 6 hrs. After concentration under reduced pressure, the residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=7:3→3:7→basic silica gel, hexane:ethyl acetate=1:1→ethyl acetate) to give the title compound (1.05 g) as colorless crystals.

Workup

  1. temperatureheated at 50° C.
  2. stirringthe mixture was stirred for 6 hrs
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was separated
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=7:3→3:7→basic silica gel, hexane:ethyl acetate=1:1→ethyl acetate)

Sources & evidence

ORD record
ord-c2d3debbf272486b9297c72bde07014f
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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