Ethanol → HCID 67202157, compound

HRID 853250Notes

Reaction equation

HRID 853250 reaction equation
[Cl-].[NH4+].C(O)C.O.[N+:7]([C:10]1[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=1[O:12][C:13]1[C:14]2[C:21]([CH3:22])=[C:20]([CH3:23])[NH:19][C:15]=2[N:16]=[CH:17][N:18]=1)([O-])=O>[Fe].C(OCC)(=O)C.O1CCCC1>[NH2:7][C:10]1[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=1[O:12][C:13]1[C:14]2[C:21]([CH3:22])=[C:20]([CH3:23])[NH:19][C:15]=2[N:16]=[CH:17][N:18]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 67202106HCID 67202106, compound

Product 1

HCID 67202157HCID 67202157, compoundYield 30.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding iron powder (0.1 g), ammonium chloride (0.2 g), ethanol (4 ml) and water (1 ml) to the 4-(nitrophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine (80 mg) synthesized by the intermediate synthesis method described above, the mixture was stirred at 75–82° C. for 1.5 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 the organic layer was washed with water and saturated brine in that order, dried over sodium sulfate, concentrated to dryness under reduced pressure and washed with diethyl ether to obtain the title compound (22 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
  5. washthe organic layer was washed with water and saturated brine in that order
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-732a21ec38d645d3a17a51936cf9595e
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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