Triethylamine → HCID 89579370, compound

HRID 928572Notes

Reaction equation

HRID 928572 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:17]([O:20][CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[C:18]#[CH:19].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.O.[Cu]I>[C:11]1([C:10]2[C:3]3[C:2]([C:19]#[C:18][CH2:17][O:20][CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)=[N:7][CH:6]=[N:5][C:4]=3[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 7087304-Chloro-5-phenylthieno[2,3-d]pyrimidineHCID 87814959HCID 87814959, compound

Product 1

HCID 89579370HCID 89579370, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Nitrogen gas was bubbled through a mixture of 4-chloro-5-phenyl-thieno[2,3-d]pyrimidine (1 g, 4.06 mmol), 1-(2-prop-2-ynoxyethyl)pyrrolidine (1.53 g, 10 mmol), bistriphenylphosphine palladium (II) dichloride (180 mg, 0.25 mmol), triethylamine (3.5 mL, 25 mmol), copper (I) iodide (75 mg, 0.4 mmol) in THF (20 mL) for 5 minutes. The reaction was then heated at 100° C. for 60 minutes in a microwave. The reaction was then diluted with ethyl acetate (50 ml) and water (50 ml) and shaken. The ethyl acetate layer was then separated, dried over sodium sulphate and concentrated in vacuum to a gum. The gum was chromatographed on silica in a gradient of 2-15% methanol in dichloromethane. A peak eluted in about 8-12% methanol in dichloromethane to give 5-phenyl-4-[3-(2-pyrrolidine-1-ylethoxy)prop-1-ynyl]thieno[2,3-d]pyrimidine as a gum. (55 mg, 0.15 mmol, 3.7%). LCMS [M+H]+=364; RT=3.04 min.

Workup

  1. customThe ethyl acetate layer was then separated
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuum to a gum
  4. customThe gum was chromatographed on silica in a gradient of 2-15% methanol in dichloromethane
  5. washA peak eluted in about 8-12% methanol in dichloromethane

Sources & evidence

ORD record
ord-1158ff429f164d16b3d76a3bbef4ae06
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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