Triethylamine → HCID 78167188, compound

HRID 2278871Notes

Reaction equation

HRID 2278871 reaction equation
[Cl:1][C:2]1[N:10]=[C:9](I)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH3:12].C(N(CC)CC)C.[CH3:20][CH:21]([OH:24])[C:22]#[CH:23]>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[N:10]=[C:9]([C:23]#[C:22][CH:21]([OH:24])[CH3:20])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 10803775HCID 10803775, compound

Product 1

HCID 78167188HCID 78167188, compound

Reagents, catalysts & solvents 2

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

Procedure

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) were added triethylamine (4.9 ml, 34.5 mmol) and but-3-yn-2-ol (1.1 ml, 25.63 mmol). The reaction mixture was stirred at RT for 1 h. The volatiles 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 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).

Workup

  1. customThe volatiles 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. dry with materialThe combined organic phases were dried over anhydrous sodium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash chromatography (DCM/MeOH: 94/6)

Sources & evidence

ORD record
ord-2a0dcda8850c4acdb65a0f969a5020ae
Source dataset
uspto-grants-2015_09
Patent number
US09133197B2

Reaction notes

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