Potassium Carbonate → tert-butyl 4-{1-[(5-ethyl-1,3-oxazol-2-yl)methyl]-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate

HRID 1476569Notes

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.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:38][C:39]1[O:40][C:41]([CH2:44][CH3:45])=[CH:42][N:43]=1>CN(C=O)C>[CH2:44]([C:41]1[O:40][C:39]([CH2:38][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])=[N:43][CH:42]=1)[CH3:45]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (800 mg; compound B50) in DMF (15 ml) are added potassium carbonate (520 mg) and 2-(chloromethyl)-5-ethyl-1,3-oxazole (270 mg; compound D1). After stirring for 1 h at 100° C. further 2-(chloromethyl)-5-ethyl-1,3-oxazole (200 mg; compound D1) and potassium carbonate (400 mg) are added to the reaction mixture. The mixture is stirred for additional 30 min at 100° C. Afterwards all volatile materials are removed in vacuo and the residue is purified by flash chromatography [silica gel, eluent: cyclohexane/EtOAc, 3/2 (v/v)] to give the title compound as a solid.

Workup

additionare added to the reaction mixture
customAfterwards all volatile materials are removed in vacuo
customthe residue is purified by flash chromatography [silica gel, eluent: cyclohexane/EtOAc, 3/2 (v/v)]

Sources & evidence

ORD record: ord-2b87753f56864c34b5c49ae7829c7ca2
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018175B2

Reaction notes

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