Potassium Carbonate → N-[3-(4-aminophenyl)propyl]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 2102384Notes

Reaction equation

HRID 2102384 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.Cl[C:13]1[C:14]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:20][S:19][C:15]=2[N:16]=[CH:17][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.[Cu]I>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][NH:1][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[CH:20][S:19][C:15]=3[N:16]=[CH:17][N:18]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27829114-Chloro-5-(4-fluorophenyl)thieno(2,3-d)pyrimidineHCID 216466834-(3-Aminopropyl)aniline

Product 1

HCID 57803008N-[3-(4-aminophenyl)propyl]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amineYield 30%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Procedure

4-(3-aminopropyl)aniline (0.034 g, 0.23 mmol) was added to a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine (0.04 g, 0.15 mmol), copper(I) iodide (0.009 g, 0.04 mmol) and potassium carbonate (0.0626 g, 0.453 mmol) in N,N-dimethylacetamide (3 mL) and the resulting mixture was subjected to microwave radiation at 140° C. for 4 hours. The solvent was then removed by evaporation, and the residue was dissolved in ethyl acetate (50 mL), filtered, and the organics were washed with a saturated solution of sodium bicarbonate (30 mL). Concentration and purification by silica gel column chromatography (using 1-3% methanol, 0.06% ammonia in 1:1 ethyl acetate/hexane) afforded N-[3-(4-aminophenyl)propyl]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine as a white solid in 30% yield.

Workup

  1. customat 140° C.
  2. customfor 4 hours
  3. customThe solvent was then removed by evaporation
  4. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  5. filtrationfiltered
  6. washthe organics were washed with a saturated solution of sodium bicarbonate (30 mL)
  7. concentrationConcentration and purification by silica gel column chromatography (using 1-3% methanol, 0.06% ammonia in 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-34e6239ae1ea48948ba4c6365f676603
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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