Potassium Carbonate → HCID 67258349, compound

HRID 1476635Notes

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[S:34][C:35]([CH2:38][CH3:39])=[CH:36][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:38]([C:35]1[S: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])=[CH:37][CH:36]=1)[CH3:39]

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 (1.20 g, compound B50) and 2-(chloromethyl)-5-ethylthiophene (480 mg, compound D27) in dry DMF (15 ml) is added potassium carbonate (778 mg). The mixture is stirred for 1 h at 100° C. and subsequently poured into ice-cold water. After stirring for 5 min the resulting precipitate is filtered off and dried in vacuo. The residue is purified by flash column chromatography [silica gel, eluent: cyclohexane/EtOAc, 5/1 (v/v)] to afford the title compound as a solid.

Workup

additionsubsequently poured into ice-cold water
stirringAfter stirring for 5 min the resulting precipitate
filtrationis filtered off
customdried in vacuo
customThe residue is purified by flash column chromatography [silica gel, eluent: cyclohexane/EtOAc, 5/1 (v/v)]

Sources & evidence

ORD record: ord-fbebc9152bec4e90af832c358c2cf166
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018175B2

Reaction notes

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