Triethylamine → HCID 71745308, compound

HRID 2278866Notes

Reaction equation

HRID 2278866 reaction equation
CCN(CC)CC.[CH2:8]([OH:12])[CH2:9][C:10]#[CH:11].[Cl:13][C:14]1[N:22]=[C:21](I)[N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[CH3:24]>O1CCOCC1.[Cu]I>[Cl:13][C:14]1[N:22]=[C:21]([C:11]#[C:10][CH2:9][CH2:8][OH:12])[N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 10803775HCID 10803775, compound

Product 1

HCID 71745308HCID 71745308, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

NEt3 (4.9 ml, 34.5 mmol) and but-3-yn-1-ol (1.1 ml, 25.63 mmol) were added to a solution of 6-chloro-2-iodo-9-methyl-9H-purine (6.8 g, 23.3 mmol), CuI (454 mg, 2.23 mmol) and bis-triphenylphosphine palladium dichloride (811 mg, 1.15 mmol) in dioxane (93 ml). The reaction mixture was stirred at RT for 1 h. The solvents were removed under reduced pressure. Water (50 ml) was added to the dark residue obtained. The aqueous phase was extracted with DCM (3×100 ml). The combined organic phases were dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residue was purified by flash chromatography (DCM/MeOH: 94/6) to give an off-white precipitate.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionWater (50 ml) was added to the dark residue
  3. customobtained
  4. extractionThe aqueous phase was extracted with DCM (3×100 ml)
  5. dry with materialThe combined organic phases were dried over anhydrous sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (DCM/MeOH: 94/6)
  8. customto give an off-white precipitate

Sources & evidence

ORD record
ord-3532ba1c33c84a679a2b27dfd34ebc47
Source dataset
uspto-grants-2015_09
Patent number
US09133197B2

Reaction notes

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