Triethylamine → HCID 57714143, compound

HRID 1984247Notes

Reaction equation

HRID 1984247 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](=[O:14])[N:11]([CH2:15][C:16]#[CH:17])[C:10](=[O:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:20]1[C:21]([NH:28][CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[N:22][C:23]([C:26]#[N:27])=[N:24][CH:25]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C=O)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>[CH2:1]([N:8]1[CH2:9][C:10](=[O:18])[N:11]([CH2:15][C:16]#[C:17][C:20]2[C:21]([NH:28][CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[N:22][C:23]([C:26]#[N:27])=[N:24][CH:25]=2)[C:12](=[O:14])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrileHCID 57714139HCID 57714139, compound

Product 1

HCID 57714143HCID 57714143, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-benzyl-1-prop-2-ynyl-piperazine-2,6-dione (1.5 mmol) and 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (1 mmol) in DMF (5 ml), triethylamine (3.0 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.1 mmol) and copper (I) iodide (0.2 mmol) are added. The reaction mixture is heated at 85° C. ca. for 1 day. Saturated aqueous solution of ammonium chloride is added to the reaction mixture and then aqueous layer is extracted with two 50 ml portions of AcOEt. The combined extracts are washed with brine, dried over magnesium sulfate and concentrated under vacuum to give crude product, which is purified by silica gel column chromatography. Yield: 93%. Rf=0.3 (AcOEt only)

Workup

  1. extractionaqueous layer is extracted with two 50 ml portions of AcOEt
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give crude product, which
  6. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2f7d3455a93410f91fac00c4d61b2da
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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