Potassium Carbonate → N-(3-{3-[(5-phenylthieno[2,3-d]pyrimidin-4-yl)oxy]propoxy}phenyl)acetamide

HRID 2102386Notes

Reaction equation

HRID 2102386 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](=[O:16])[N:13]=[CH:12][NH:11][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]1([C:7]2[C:15]3[C:14]([O:16][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=4)=[N:13][CH:12]=[N:11][C:10]=3[S:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6420330N-[3-(3-Bromo-propoxy)-phenyl]-acetamideHCID 178518230HCID 178518230, compound

Product 1

HCID 11690276N-(3-{3-[(5-phenylthieno[2,3-d]pyrimidin-4-yl)oxy]propoxy}phenyl)acetamideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-phenylthieno[2,3-d]pyrimidin-4(1H)-one (0.023 g, 0.10 mmol), N-[3-(3-bromopropoxy)phenyl]acetamide (0.0274 g, 0.10 mmol), potassium carbonate (0.0418 g, 0.30 mmol) and N,N-dimethylformamide (1.0 mL) was heated to 90° C. for 6 h. The reaction was then allowed to cool to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate (30 mL), water (30 mL) was added, and the organic layer was separated, Concentration, followed by followed by silica gel column chromatography purification (using 1.50% methanol in 1:1 ethyl acetate/hexane and ammonia (0.03%) as eluent) afforded N-(3-{3-[(5-phenylthieno[2,3-d]pyrimidin-4-yl)oxy]propoxy}phenyl)acetamide in 66% yield. N-{4-[3-(4-oxo-5-phenylthieno[2,3-d]pyrimidin-1(4H)-yl)propoxy]phenyl}acetamide was also formed in 12% yield during the reaction.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  4. additionwater (30 mL) was added
  5. customthe organic layer was separated
  6. concentrationConcentration
  7. customby followed by silica gel column chromatography purification (using 1.50% methanol in 1:1 ethyl acetate/hexane and ammonia (0.03%) as eluent)

Sources & evidence

ORD record
ord-001619246a8441bb8b6609840f02157d
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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