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

HRID 1476638Notes

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:31]([C:35]1[O:36][C:37]([CH2:40]Cl)=[N:38][N:39]=1)([CH3:34])([CH3:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:31]([C:35]1[O:36][C:37]([CH2:40][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:38][N:39]=1)([CH3:34])([CH3:33])[CH3:32]

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 (2.565 g, compound B50) and 2-tert-butyl-5-(chloromethyl)-1,3,4-oxadiazole (1050 mg, compound D29) in dry DMF (50 ml) is added potassium carbonate (829 mg). The mixture is stirred for 3 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 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

Sources & evidence

ORD record: ord-8d6067b328d542288b645da9131d7fc4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018175B2

Reaction notes

Loading…