2-Methoxyaniline → 2-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamide
Reaction equation
ClC1N=C(C(OCC)=O)C([N+]([O-])=O)=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])N=1.Cl[C:26]1[N:31]=[C:30]([C:32]([O:34]CC)=O)[C:29]([N+:37]([O-])=O)=[C:28](Cl)[N:27]=1.C[O:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1N.C([N:53](C(C)C)CC)(C)C>O1CCCC1>[OH:42][C:43]1[CH:44]=[C:46]([C:26]2[N:27]=[C:28]3[C:29]([N:37]=[CH:4][N:16]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])=[C:30]([C:32]([NH2:53])=[O:34])[N:31]=2)[CH:47]=[CH:48][CH:49]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. In a 250 mL round-bottomed flask was placed ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (2 g, 7.52 mmol) in tetrahydrofuran (50 mL) and the mixture was cooled down to −78° C. A solution of 2-methoxyaniline (0.763 mL, 6.77 mmol) and diisopropylethyl amine (1.313 mL, 7.52 mmol) in 4 mL of tetrahydrofuran was added dropwise and the reaction was allowed to warm to room temperature overnight. Solvent was removed under reduced pressure and the crude material was purified by column chromatography (SiO2, 90% nHexanes in ethyl acetate) to provide the title compound as an orange solid (2.42 g, 6.86 mmol, 91% yield). MS (ESI) m/z 353.3 [M+1]+.
Workup
- customIn a 250 mL round-bottomed flask was placed
- customSolvent was removed under reduced pressure
- customthe crude material was purified by column chromatography (SiO2, 90% nHexanes in ethyl acetate)
Sources & evidence
- ORD record
- ord-134e323cc05541a99db0158b9c620909
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383634B2
Reaction notes
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