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

HRID 1476580Notes

Reaction equation

HRID 1476580 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][CH:35]=[C:36]([CH3:38])[N:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:38][C:36]1[N:37]=[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:34][CH:35]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112750912-(Chloromethyl)-4-methyl-1,3-thiazoleHCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

Product 1

HCID 67258239tert-butyl 4-{1-[(4-methyl-1,3-thiazol-2-yl)methyl]-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (855 mg; compound B50) is reacted with 2-(chloromethyl)-4-methyl-1,3-thiazole (368 mg; compound D13) in the presence of potassium carbonate (276 mg) in DMF (15 ml). Using WU1 a solid is obtained which is purified by flash chromatography [silica gel, eluation gradient: DCM/MeOH, 100/0 to 95/5 (v/v)] to give the title compound as a solid.

Workup

  1. customis obtained which
  2. customis purified by flash chromatography [silica gel, eluation gradient: DCM/MeOH, 100/0 to 95/5 (v/v)]

Sources & evidence

ORD record
ord-8e8b0df9cf4b41ed9c7009e19cef3739
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

Loading…