Sodium Iodide → 3-[4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-butyl]thieno[3,4-d]pyrimidine-2,4-dione

HRID 2165208Notes

Reaction equation

HRID 2165208 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[C:14]([C:15]([O:17]C)=O)=[CH:13][S:12][CH:11]=1)=[O:8].Cl.[F:20][C:21]1[CH:34]=[CH:33][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+].[I-].[Na+].NC1C(C(OC)=O)=CSC=1.BrCCCCN=C=O>C(O)(C)C.C1(C)C=CC=CC=1>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:15](=[O:17])[C:14]4=[CH:13][S:12][CH:11]=[C:10]4[NH:9][C:7]3=[O:8])[CH2:29][CH2:28]2)=[O:26])=[CH:33][CH:34]=1

Participants

9

Reactant 6

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 2777610Methyl 4-aminothiophene-3-carboxylateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 149715841-Bromo-4-isocyanatobutaneHCID 15697666N-(4-bromobutyl)-N'-(4-carbomethoxythien-3-yl)urea

Product 1

HCID 145004063-[4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-butyl]thieno[3,4-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by dissolving N-(4-bromobutyl)-N'-(4-carbomethoxythien-3-yl)urea (6.92g, 21 mmol) in isopropanol (100 ml) and then successively treating the solution with 4-(4-fluorobenzoyl)piperidine hydrochloride (10.16 g, 42 mmol), sodium bicarbonate (3.7 g, 44 mmol) and sodium iodide (1.90 g, 12 mmol) to form a mixture. The urea was prepared by reacting methyl 4-aminothiophene-3-carboxylate with 4-bromobutylisocyanate in toluene at room temperature for 12 hours to produce the urea as a tan solid, mp 85°-86° C. The mixture was then heated to reflux under a nitrogen atmosphere for 12 hours. The reaction mixture was reduced to half volume, diluted with water, and concentrated to remove the remainder of the alcohol solvent. The residue was extracted with methylene chloride and the combined organic extracts were dried with saturated brine and magnesium sulfate. After concentration of the extracts, the residue was purified on silica gel using methylene chloride/ethanol/ammonium hydroxide (96:3.5:0.5) as eluant. There was obtained 3.62 g (40.8% yield) of the title compound as a brown solid. This material was recrystallized from CH2Cl2 /ether, mp 190°-192° C.

Workup

  1. customThe title compound was prepared
  2. customto form a mixture
  3. customThe urea was prepared
  4. customat room temperature
  5. customfor 12 hours

Sources & evidence

ORD record
ord-d3d6e94072044445b35b2d1da6b7dff0
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

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