Citric Acid → Benzyl 3-{4-[5-(3-chlorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}cyclobutanecarboxylate

HRID 1027716Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.CS([C:19]1[N:20]=[CH:21][C:22]2[N:27]=[C:26]([C:28]3[CH:48]=[C:47]([CH3:49])[C:31]([O:32][CH:33]4[CH2:36][CH:35]([C:37]([O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[O:38])[CH2:34]4)=[C:30]([CH3:50])[CH:29]=3)[O:25][C:23]=2[N:24]=1)(=O)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:19]1[N:20]=[CH:21][C:22]2[N:27]=[C:26]([C:28]3[CH:29]=[C:30]([CH3:50])[C:31]([O:32][CH:33]4[CH2:36][CH:35]([C:37]([O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[O:38])[CH2:34]4)=[C:47]([CH3:49])[CH:48]=3)[O:25][C:23]=2[N:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

48 mg of potassium carbonate and 20 mg of 3-chlorophenol were added to a solution of 70 mg of benzyl 3-[4-(5-methanesulfonyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]cyclobutanecarboxylate in 5 ml of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 1.5 h and at 60° C. for a further 4 h. For work-up, 10% strength aqueous citric acid solution was added, and the reaction was extracted with dichloromethane. The combined organic phases were concentrated and dried under reduced pressure. This gave 77 mg (100%) of the title compound, which was reacted further without any purification.

Workup

extractionthe reaction was extracted with dichloromethane
concentrationThe combined organic phases were concentrated
customdried under reduced pressure
customThis gave 77 mg (100%) of the title compound, which was reacted further without any purification

Sources & evidence

ORD record: ord-d1aea7276bd4416d8bf60e95a8db2d27
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735402B2

Reaction notes

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