Potassium Carbonate → HCID 67259055, compound

HRID 1476589Notes

Reaction equation

HRID 1476589 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:37][N:36]=[C:35]([CH2:38][CH3:39])[N:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:38]([C:35]1[N: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])[S:37][N:36]=1)[CH3:39]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylateHCID 672580541312601-20-92×

Product 1

HCID 67259055HCID 67259055, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

According to GP1 tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (563 mg; compound B50) is reacted with 5-(chloromethyl)-3-ethyl-1,2,4-thiadiazole (226 mg; compound D20) in the presence of potassium carbonate (364 mg) in DMF (10 ml). After 3 h and additionally after 6 h at 100° C. additional 5-(chloromethyl)-3-ethyl-1,2,4-thiadiazole (214 mg and 107 mg; compound D20) in DMF (5 ml each) is added, and the mixture is stirred at 100° C. for another 5 h. Using WU2 the title compound is obtained after flash column chromatography [silica gel, eluent: cyclohexane/EtOAc, 3/1 (v/v)] as a solid.

Sources & evidence

ORD record
ord-1e325cf126764e38aec4904eaf94a026
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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