Ethanol → 5-(4-Aminophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 227609Notes

Reaction equation

HRID 227609 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)C>C1COCC1.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 597942485-(4-Nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 250237745-(4-Aminophenyl)thieno[2,3-d]pyrimidin-4-amineYield 97.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of Example 58C (0.5 g, 1.83 mmol) in THF (30 mL), water (15 mL), and ethanol (40 mL) was heated to 50° C., treated with iron powder (0.616 g, 11.02 mmol), heated to between 70 and 80° C. for two hours, and filtered while hot through diatomaceous earth (Celite®). The pad was washed with TBF (10 mL) and ethanol and the combined filtrates were concentrated. The residue was partitioned between water and ethyl acetate and the aqueous phase was extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to give 0.432 g of the desired product. MS (CI) m/e 243 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.30 (s, 1H); 7.28 (s, 1H); 7.11 (d, J=8.4 Hz, 2H); 6.68 (d, J=8.4 Hz, 2H); 5.39 (br s, 2H).

Workup

  1. temperatureheated to between 70 and 80° C. for two hours
  2. filtrationfiltered while hot through diatomaceous earth (Celite®)
  3. washThe pad was washed with TBF (10 mL) and ethanol
  4. concentrationthe combined filtrates were concentrated
  5. customThe residue was partitioned between water and ethyl acetate
  6. extractionthe aqueous phase was extracted three times with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f23060ba9910479984dc57b40ae9d09e
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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