N,N,N',N'-Tetramethylethylenediamine → HCID 71239559, compound

HRID 1403231Notes

Reaction equation

HRID 1403231 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([NH2:31])=[O:30])[CH:9]=2)[C:5]([C:32]#[CH:33])=[CH:4][N:3]=1.I[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CN(C)CCN(C)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>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([NH2:31])=[O:30])[CH:9]=2)[C:5]([C:32]#[C:33][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 11575IodobenzeneHCID 86725298HCID 86725298, compound

Product 1

HCID 71239559HCID 71239559, compoundYield 65.2%

Reagents, catalysts & solvents 3

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

Procedure

In a sealed tube filled with argon, a mixture of 5-(2-amino-5-ethynylpyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (120 mg, 0.25 mmol), Pd(PPh3)2Cl2 (21 mg, 0.03 mmol), CuI (6 mg, 0.03 mmol), iodobenzene (153 mg, 0.75 mmol) and TEA (0.348 mL, 2.5 mmol) in degassed ACN (2.5 mL) was stirred at room temperature overnight. To the reaction mixture was added N,N,N′,N′-tetramethylethylenediamine (0.075 mL, 0.5 mmol) and the reaction mixture stirred at the same temperature for 15 min. The solvent was evaporated under vacuum and the residue purified by flash chromatography (hexane/EtOAc 1/1+1% TEA), to obtain the title compounds (91 mg, 65%).

Workup

  1. additionIn a sealed tube filled with argon
  2. stirringthe reaction mixture stirred at the same temperature for 15 min
  3. customThe solvent was evaporated under vacuum
  4. customthe residue purified by flash chromatography (hexane/EtOAc 1/1+1% TEA)

Sources & evidence

ORD record
ord-8e30f622ca284e27a4773d5e290e0d0c
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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