1-Bromo-3-chloropropane → 1-(3-chloropropyl)-5-(2-thienyl)-2,4(1H,3H)-pyrimidinedione

HRID 1661060Notes

Reaction equation

HRID 1661060 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7](=[O:13])[NH:8][C:9](=[O:12])[NH:10][CH:11]=1.Br[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:18][CH2:17][CH2:16][CH2:15][N:10]1[CH:11]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:7](=[O:13])[NH:8][C:9]1=[O:12]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 8190965-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 593375931-(3-chloropropyl)-5-(2-thienyl)-2,4(1H,3H)-pyrimidinedioneYield 21.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione (Prep22, 1 g, 5.15 mmol), 1-bromo-3-chloropropane (0.81 g, 5.15 mmol) and potassium carbonate (0.71 g, 5.15 mmol) in DMF (10 ml) was stirred at room temperature for 7 hours, then the mixture was diluted with water and extracted with ethyl acetate. Organic phase was evaporated and the crude was purified by a FC (eluent P:E=3:1, 1:1) to afford the title compound (300 mg, y=21%)

Workup

  1. extractionextracted with ethyl acetate
  2. customOrganic phase was evaporated
  3. customthe crude was purified by a FC (eluent P:E=3:1, 1:1)

Sources & evidence

ORD record
ord-50f7db5ca52b42c18339f6c0c25a4050
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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