Ethanol → 4-(3-Aminophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine

HRID 1433394Notes

Reaction equation

HRID 1433394 reaction equation
[Cl-].[NH4+].C(O)C.O.[N+:7]([C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[O:13][C:14]1[C:15]2[C:22]([CH3:23])=[C:21]([CH3:24])[NH:20][C:16]=2[N:17]=[CH:18][N:19]=1)([O-])=O>[Fe].C(OCC)(=O)C.O1CCCC1>[NH2:7][C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[O:13][C:14]1[C:15]2[C:22]([CH3:23])=[C:21]([CH3:24])[NH:20][C:16]=2[N:17]=[CH:18][N:19]=1

Participants

8

Conditions

Temperature
85 °C

Procedure

After adding iron powder (0.12 g), ammonium chloride (0.24 g), ethanol (5 ml) and water (1 ml) to the 4-(3-nitrophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine (110 mg) synthesized by the intermediate synthesis method described above, the mixture was stirred at 80-90° C. for 3 hours. After returning the reaction system to room temperature and adding tetrahydrofuran (3 ml) and ethyl acetate (3 ml), the mixture was filtered with celite, the filtrate was subjected to liquid separation and extraction with ethyl acetate, and the organic layer was washed with water and saturated brine in that order. It was then dried over sodium sulfate, concentrated to dryness under reduced pressure and washed with diethyl ether to obtain the title compound (37 mg).

Workup

  1. customsynthesized by the intermediate synthesis method
  2. customto room temperature
  3. filtrationthe mixture was filtered with celite
  4. customthe filtrate was subjected to liquid separation and extraction with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine in that order
  6. dry with materialIt was then dried over sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-14c960d9b6dc4a86a06daacd69c81b28
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

Loading…