Trimethylsilylacetylene → HCID 68934762, compound

HRID 1878622Notes

Reaction equation

HRID 1878622 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH:23]=[CH:22][NH:21][C:10]=3[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=3)[N:13]=2)[CH:5]=[N:6][CH:7]=1.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26]>[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>[CH3:20][C:16]1[N:15]=[C:14]([C:12]2[N:13]=[C:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[CH:3]=3)[C:9]3[CH:23]=[CH:22][NH:21][C:10]=3[N:11]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 441944484-(5-Bromo-pyridin-3-yl)-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 68934762HCID 68934762, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

To a suspension of of 4-(5-bromo-pyridin-3-yl)-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (Example 16) (1 eq, 0.451 mmol, 250 mg) in TEA/DMF (1:1, 6 ml) are added copper (I) iodide (0.1 eq, 0.045 mmol, 8.8 mg), PdCl2(PPh3)2 (0.1 eq, 0.045 mmol, 32.3 mg), and trimethylsilylacetylene (Sigma-Aldrich, St. Louis, USA) (1.5 eq, 0.68 mmol, 0.098 ml). The resulting mixture is stirred at 90° C. for 1 h. The solvents are removed in vacuo, then sat. aqueous NaHCO3 solution is added, and the mixture is extracted with EtOAc. The organic layer is washed with sat. aqueous NaCl solution, dried with MgSO4, and concentrated under reduced pressure. The crude product is purified by reversed phase HPLC and recrystallized in EtOAc giving the title compound; [M+H]+=384.

Workup

  1. customThe solvents are removed in vacuo
  2. additionsat. aqueous NaHCO3 solution is added
  3. extractionthe mixture is extracted with EtOAc
  4. washThe organic layer is washed with sat. aqueous NaCl solution
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by reversed phase HPLC
  8. customrecrystallized in EtOAc giving the title compound

Sources & evidence

ORD record
ord-8e99d8dbda5b4196a8ef3d195d6daecd
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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