Triethylamine → 4-Cyclopentylamino-5-(4-phenyl-but-1-ynyl)-pyrimidine-2-carbonitrile

HRID 1163008Notes

Reaction equation

HRID 1163008 reaction equation
Br[C:2]1[C:3]([NH:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:16]1([CH2:22][CH2:23][C:24]#[CH:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.[Cl-].[NH4+]>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>[CH:11]1([NH:10][C:3]2[C:2]([C:25]#[C:24][CH2:23][CH2:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:7][N:6]=[C:5]([C:8]#[N:9])[N:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 1233604-Phenyl-1-butyneHCID 686474045-Bromo-4-cyclopentylamino-pyrimidine-2-carbonitrile

Product 1

HCID 102452344-Cyclopentylamino-5-(4-phenyl-but-1-ynyl)-pyrimidine-2-carbonitrileYield 89.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

5-Bromo-4-cyclopentylamino-pyrimidine-2-carbonitrile (0.69 mmol), 4-phenyl-1-butyne (1.66 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.035 mmol), copper (I) iodide (0.07 mmol) and triethylamine (2.1 mmol) in D (5 ml) is stirred at 75° C. for 2.5 h. The reaction mixture is treated with saturated ammonium chloride and extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. The crude product is applied to a silica gel column chromatography, which is eluted with following solvents: n-hexane:AcOEt=12:1 (v/v) and n-hexane:AcOEt=10:1 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 89.9%, Rf=0.65 (n-hexane:AcOEt=2:1). 1H-NMR (400 MHz, CDCl3) δ 1.26-1.33 (m, 2H), 1.64-1.71 (m, 4H), 2.05-2.09 (m, 3H), 2.79-2.86 (m, 2H), 2.94-3.00 (m, 2H), 4.30-4.38 (m, 2H), 5.36-5.34 (m, 1H), 7.35-7.21 (m, 5H), 8.10 (s, 1H),

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down
  5. washis eluted with following solvents
  6. customThe solvent of the latter effluent is removed by evaporation
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9e4594239c634b6891bbafd8b16eadac
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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