Potassium Carbonate → ethyl 2-((1S,4S)-5-benzhydryl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyrimidine-5-carboxylate

HRID 718063

Reaction equation

Cl.Cl.[CH:3]([N:16]1[CH2:21][C@@H:20]2[CH2:22][C@H:17]1[CH2:18][NH:19]2)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS([C:27]1[N:32]=[CH:31][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:28]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[CH:3]([N:16]1[CH2:21][C@@H:20]2[CH2:22][C@H:17]1[CH2:18][N:19]2[C:27]1[N:28]=[CH:29][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][N:32]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Title compound 201 (0.250 g, 0.741 mmol), ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (0.122 g, 0.529 mmol), potassium carbonate (0.280 g, 2.645 mmol) and DME (5 mL) were combined. The reaction mixture was stirred at 50° C. for 2 hours. The mixture was cooled down and quench with water. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography eluting with 0% to 30% ethyl acetate in hexanes to afford title compound 202 (0.141 g, 64%). LRMS (ESI): (calc) 414.21. (found) 415.0 (MH)+.

Workup

temperatureThe mixture was cooled down
customquench with water
extractionThe aqueous layer was extracted twice with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude was purified by flash chromatography
washeluting with 0% to 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-06bd3d9ed7584b46ab8c3fa83ab5602e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193749B2

Linked notes

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