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

HRID 1476660Notes

Reaction equation

HRID 1476660 reaction equation
[Br:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6](=[O:25])[NH:5][C:4]=2[CH:3]=1.Cl[CH2:27][C:28]1[O:32][N:31]=[C:30]([CH2:33][O:34][CH3:35])[N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]3)[C:6](=[O:25])[N:5]([CH2:27][C:28]3[O:32][N:31]=[C:30]([CH2:33][O:34][CH3:35])[N:29]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 252192435-(Chloromethyl)-3-(methoxymethyl)-1,2,4-oxadiazoleHCID 67258027tert-butyl 4-(6-bromo-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

Product 1

HCID 67259367tert-butyl 4-[6-bromo-1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the procedure describe for compound B99 of tert-butyl 4-(6-bromo-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (10.00 g; compound B53) is reacted with 5-(chloromethyl)-3-(methoxymethyl)-1,2,4-oxadiazole (3.78 g, D14) in the presence of potassium carbonate (3.21 g) in DMF (93 ml) to afford the title compound as a solid.

Sources & evidence

ORD record
ord-694970c481e7435fa066bb93ca16efc5
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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