Ethanol → 4-(3-Aminophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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
- customsynthesized by the intermediate synthesis method
- customto room temperature
- filtrationthe mixture was filtered with celite
- customthe filtrate was subjected to liquid separation and extraction with ethyl acetate
- washthe organic layer was washed with water and saturated brine in that order
- dry with materialIt was then dried over sodium sulfate
- concentrationconcentrated to dryness under reduced pressure
- washwashed with diethyl ether
Sources & evidence
- ORD record
- ord-6859366c0f554e42b2ad4ce7be925126
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253286B2
Reaction notes
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