Triethylamine → 6-((1H-imidazol-1-yl)methyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271554Notes

Reaction equation

HRID 271554 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)[C:2]#[CH:3].Br[C:10]1[C:11]([NH:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=1.C(N(CC)CC)C>CN(C=O)C.O.CCOC(C)=O.[Cu]I.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>[CH3:21][C:20]([CH3:23])([CH3:22])[CH2:19][N:18]1[C:11]2[N:12]=[C:13]([C:16]#[N:17])[N:14]=[CH:15][C:10]=2[CH:3]=[C:2]1[CH2:1][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 125919421-(prop-2-yn-1-yl)-1H-imidazoleHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrile

Product 1

HCID 99439696-((1H-imidazol-1-yl)methyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileYield 64%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-Prop-2-ynyl-1H-imidazole (15 mmol) is dissolved in DMF at room temperature under nitrogen atmosphere. To the solution, 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (8 mmol), triethylamine (24 mmol), copper(I) iodide (0.8 mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.4 mmol) are added successively. The mixture is heated at 80° C. under nitrogen atmosphere for 3 h. After cooling at room temperature, the mixture is diluted with H2O and AcOEt and filtered with celite. The organic layer is taken, dried over MgSO4 and evaporated in vacuo. The residue is purified by silica gel column chromatography (AcOEt:MeOH=20:1) to give 7-(2,2-dimethyl-propyl)-6-imidazol-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 64% yield.

Workup

  1. temperatureAfter cooling at room temperature
  2. filtrationfiltered with celite
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue is purified by silica gel column chromatography (AcOEt:MeOH=20:1)

Sources & evidence

ORD record
ord-b5be8e59fee24362b77d64a6ebe13980
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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