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

HRID 1476659Notes

Reaction equation

HRID 1476659 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.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:33][C:34]1[O:38][N:37]=[C:36]([CH2:39][CH3:40])[N:35]=1>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]([CH2:33][C:34]3[O:38][N:37]=[C:36]([CH2:39][CH3:40])[N:35]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162279165-(Chloromethyl)-3-ethyl-1,2,4-oxadiazole2×HCID 67258027HCID 67258027, compound

Product 1

HCID 67258967Tert-butyl 4-{6-bromo-1-[(3-ethyl-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

Conditions

Temperature
100 °C

Procedure

Tert-butyl 4-(6-bromo-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (5.00 g, compound B53) and potassium carbonate (1.60 g) are suspended in dry DMF (50 ml) and 5-(chloromethyl)-3-ethyl-1,2,4-oxadiazole (1.70 g, compound D7) is added. The reaction mixture is stirred at 100° C. for 2 h and then poured into ice-cold water (250 ml). The resulting precipitate is filtered off and dried in vacuo to afford the title compound as a solid.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. customdried in vacuo

Sources & evidence

ORD record
ord-f2a714bef449416da7d8fe0593b9f64d
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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