Hydrochloric Acid → 1-(4-chlorobutyl)-5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione

HRID 1661059Notes

Reaction equation

HRID 1661059 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][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C(OCC)(=O)C.O>[Cl:19][CH2:18][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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 8190965-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 592339261-(4-chlorobutyl)-5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dioneYield 22%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione (Prep22, 2.5 g, 12.9 mmol), 1-bromo-4-chlorobutane (2.2 g, 12.9 mmol) and potassium carbonate (1.8 g, 12.9 mmol) in DMF (150 ml) was stirred at room temperature for 5 hours. Water was added and the solution was adjusted to pH=6 with 3N hydrochloride acid. Ethyl acetate was added and the aqueous layer was extracted three times, the combined organic layer was dried and concentrated, the residue was purified by FC(P:E=3:1) to give the title compound (800 mg, y=22%).

Workup

  1. extractionthe aqueous layer was extracted three times
  2. customthe combined organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was purified by FC(P

Sources & evidence

ORD record
ord-9c972d6e0d034f4cba67c0b81720521f
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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