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

HRID 1010129Notes

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

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

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-ff15f5cc3a334f448e299e8a17cf3c7b
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973160B2

Reaction notes

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