Potassium Carbonate → HCID 67258559, compound

HRID 1476578Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:5]=2[C:4](=[O:17])[N:3]1[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.Cl[CH2:32][C:33]1[O:37][N:36]=[C:35]([CH2:38][S:39][CH3:40])[N:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:40][S:39][CH2:38][C:35]1[N:34]=[C:33]([CH2:32][N:7]2[C:6]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[S:10][C:5]=3[C:4](=[O:17])[N:3]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[C:2]2=[O:1])[O:37][N:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

According to GP1 tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (1 g; compound B50) is reacted with 5-(chloromethyl)-3-[(methylsulfanyl)methyl]-1,2,4-oxadiazole (410 mg; compound D11) in the presence of potassium carbonate (320 mg) in DMF (20 ml). The reaction mixture is stirred at 100° C. for 1 h. Ice cold water is added and the mixture is extracted with DCM 4 times. The combined organic layers are dried (sodium sulfate) and concentrated in vacuo. The residue is purified by flash column chromatography [silica gel, eluation gradient: cyclohexane/EtOAc, 1/0 to 1/1 (v/v)] to afford the title compound as a solid.

Workup

additionIce cold water is added
extractionthe mixture is extracted with DCM 4 times
dry with materialThe combined organic layers are dried (sodium sulfate)
concentrationconcentrated in vacuo
customThe residue is purified by flash column chromatography [silica gel, eluation gradient: cyclohexane/EtOAc, 1/0 to 1/1 (v/v)]

Sources & evidence

ORD record: ord-3b1953f2ed974acc998a17c935678ac1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018175B2

Reaction notes

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