N,N,N',N'-Tetramethylethylenediamine → HCID 86725296, compound

HRID 1403228Notes

Reaction equation

HRID 1403228 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]([O:31][CH2:32][CH3:33])=[O:30])[CH:9]=2)[C:5](I)=[CH:4][N:3]=1.[C:35]([Si:37]([CH3:40])([CH3:39])[CH3:38])#[CH:36].C(N(CC)CC)C.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]([CH3:20])([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]([O:31][CH2:32][CH3:33])=[O:30])[CH:9]=2)[C:5]([C:36]#[C:35][Si:37]([CH3:40])([CH3:39])[CH3:38])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 71239649HCID 71239649, compound

Product 1

HCID 86725296HCID 86725296, compoundYield 85%

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 ethyl 5-(2-amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylate (612 mg, 1.0 mmol), Pd(PPh3)2Cl2 (70 mg, 0.1 mmol), CuI (19 mg, 0.1 mmol), ethynyl(trimethyl)silane (0.415 mL, 3 mmol) and triethylamine (10 mmol) in degassed ACN (10 mL) was stirred at room temperature overnight. To the reaction mixture was added N,N,N′,N′-tetramethylethylenediamine (0.3 mL, 2 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 8/2) to obtain the title compound (495 mg, 85%).

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 8/2)

Sources & evidence

ORD record
ord-6a26afccc7fb4655a1e1cd2d28790dc0
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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