Triethylamine → HCID 70373666, compound

HRID 1524341Notes

Reaction equation

HRID 1524341 reaction equation
C[Si]([C:5]#[CH:6])(C)C.C(N(CC)CC)C.I[C:15]1[C:23]2[CH:22]=[N:21][CH:20]=[N:19][C:18]=2[N:17]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:16]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:49]([N:56]=[N+:57]=[N-:58])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1COCC1.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>[CH2:49]([N:56]1[CH:6]=[C:5]([C:15]2[C:23]3[CH:22]=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:16]=2)[N:58]=[N:57]1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 12152Benzyl azideHCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 70373442HCID 70373442, compound

Product 1

HCID 70373666HCID 70373666, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2.2 361 μl (2.61 mmol) of trimethylsilylacetylene and 402 μl (2.90 mmol) of triethylamine were added to a suspension, kept under nitrogen, of 500 mg (1.45 mmol) of tert-butyl 5-iodopyrrolo[2,3-d]pyrimidine-7-carboxylate, 19.5 mg (0.028 mmol) of bis(triphenylphosphine)palladium(II) chloride and 11.2 mg (0.059 mmol) of copper(I) iodide in 5 ml of THF, and the mixture was stirred at room temperature for 18 hours. Nitrogen was then passed through the reaction mixture for 10 minutes, and 4.4 ml of a 1 M solution of tetrabutylammonium fluoride in THF were subsequently added. After stirring at room temperature for three hours, 309 mg (2.32 mmol) of benzyl azide were added, and the reaction mixture was stirred at room temperature for 40 hours under nitrogen. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and evaporated. The residue was purified by preparative HPLC, giving tert-butyl 5-(1-benzyl-1H-1,2,3-triazol-4-yl)pyrrolo[2,3-d]pyrimidine-7-carboxylate as colourless solid; HPLC/MS: 2.23 min, [M+H] 377.

Workup

  1. waitNitrogen was then passed through the reaction mixture for 10 minutes
  2. stirringAfter stirring at room temperature for three hours
  3. stirringthe reaction mixture was stirred at room temperature for 40 hours under nitrogen
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6d4cd38b6e204f3b969ff670ffcff5f9
Source dataset
uspto-grants-2015_07
Patent number
US09079910B2

Reaction notes

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