Triethylamine → 6-Benzyl-7-isobutyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271591Notes

Reaction equation

HRID 271591 reaction equation
Br[C:2]1[C:3]([NH:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:15]1([CH2:21][C:22]#[CH:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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>[CH2:21]([C:22]1[N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]2[N:4]=[C:5]([C:8]#[N:9])[N:6]=[CH:7][C:2]=2[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 575753BenzylacetyleneHCID 179682615-Bromo-4-isobutylamino-pyrimidine-2-carbonitrile

Product 1

HCID 99658026-Benzyl-7-isobutyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileYield 40.6%

Reagents, catalysts & solvents 3

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

Procedure

5-Bromo-4-isobutylamino-pyrimidine-2-carbonitrile (0.39 mmol), 3-phenyl-1-propyne (0.78 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.02 mmol), copper (I) iodide (0.04 mmol) and triethylamine (1.2 mmol) in DMF (3 ml) is stirred at 75° C. for 2.5 h. After the reaction mixture is treated with saturated ammonium chloride, the mixture is extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. The crude product is applied to a column chromatography on silica gel, which is eluted with following solvents: n-hexane:AcOEt=10:1 (v/v) and n-hexane:AcOEt=8:1 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 40.6%, Rf=0.53 (n-hexane:AcOEt=1:1).

Workup

  1. extractionthe mixture is extracted 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-bdb808e8b9404dba937cd522a775f603
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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