Cesium carbonate → HCID 17968234, compound

HRID 271593Notes

Reaction equation

HRID 271593 reaction equation
Cl[C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[N:17]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:10]3[N:11]=[C:12]([C:15]#[N:16])[N:13]=[CH:14][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:18]1([N:17]2[C:10]3[N:11]=[C:12]([C:15]#[N:16])[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[CH2:6][C:5]2[CH:24]=[CH:25][C:2]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)=[CH:3][CH:4]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 44444199HCID 44444199, compound

Product 1

HCID 17968234HCID 17968234, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(4-chloro-benzyl)-7-cyclohexyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (1.5 mmol), 1-methylpiperazine (1.8 mmol), cesium carbonate (1.4 mmol), 2-(di-t-butylphosphino)-biphenyl (0.3 mmol) and palladium (II) acetate in toluene (6 ml) is stirred at 100° C. for 3 h. After the reaction mixture is quenched 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 silica gel column chromatography, which is eluted with following solvents: 2% MeOH in CH2Cl2 and 3% MeOH in CH2Cl2. The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 40.0%,

Workup

  1. customAfter the reaction mixture is quenched with saturated ammonium chloride
  2. extractionthe mixture is extracted with AcOEt
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down
  6. washis eluted with following solvents
  7. customThe solvent of the latter effluent is removed by evaporation
  8. customdried in vacuo

Sources & evidence

ORD record
ord-62a4143aa9bc439dbb0f8481588cb3d3
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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