Ammonium Hydroxide → 2-Chloro-5-phenylthieno[2,3-d]pyrimidine

HRID 928569Notes

Reaction equation

HRID 928569 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[NH4+].[OH-]>C(O)C.C(OCC)(=O)C.[Zn]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 127242282,4-Dichloro-5-phenylthieno(2,3-d)pyrimidine

Product 1

HCID 821046552-Chloro-5-phenylthieno[2,3-d]pyrimidineYield 29.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Dichloro-5-phenyl-thieno[2,3-d]pyrimidine (1 g, 3.56 mmol) and zinc dust (2.34 g, 35.6 mmol) were combined and stirred in ethanol (10 mL). NH4OH (1 mL) was added and the reaction heated to reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (50 mL) and filtered through celite. The filtrate was washed with water (100 mL), dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with a gradient of petroleum ether to 90/10 petroleum ether/ethyl acetate to afford 2-chloro-5-phenyl-thieno[2,3-d]pyrimidine (260 mg).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered through celite
  4. washThe filtrate was washed with water (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting residue was purified by flash chromatography
  8. washeluting with a gradient of petroleum ether to 90/10 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-47af28262fc74612a517667c877f97ff
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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