Potassium Carbonate → 1-(4-Chloro-butyl)-5-(6-methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione

HRID 12682Notes

Reaction equation

HRID 12682 reaction equation
Cl.[CH3:2][C:3]1[N:8]=[C:7]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:24]([Cl:28])[CH2:25][CH2:26][CH3:27].CC1N=C(C2C(=O)NC(=O)NC=2)C=CC=1>CN(C=O)C.O>[Cl:28][CH2:24][CH2:25][CH2:26][CH2:27][N:13]1[CH:14]=[C:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH3:2])[N:8]=2)[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 33781905-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dioneHCID 21469920Bromo-chloro-butane2×HCID 686903115-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 589942001-(4-Chloro-butyl)-5-(6-methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dioneYield 157.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

5-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 50, 50 mg, 0.208 mmol) and K2CO3 (43 mg, 0.312 mmol) were suspended in dry DMF (2 mL) and stirred for 1 h at room temperature. Then a solution of bromo-chloro-butane (71.3 mg, 0.416 mmol) in dry DMF (0.5 mL) was added dropwise and the mixture stirred for 48 hrs at room temperature. A second run of reaction was performed using 5-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione (135 mg, 0.563 mmol), K2CO3 (116 mg, 0.8445 mmol) and bromo-chloro-butane (193 mg, 1.126 mmol). After stirring the reactions at room temperature for 48 hours, the two mixtures were mixed. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated; the crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) to give the title compound as a pale yellow solid (96 mg, 43% yield).

Workup

  1. stirringthe mixture stirred for 48 hrs at room temperature
  2. customA second run of reaction
  3. stirringAfter stirring the reactions at room temperature for 48 hours
  4. additionthe two mixtures were mixed
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customthe crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2)

Sources & evidence

ORD record
ord-16bfe81ae0474d5ca77c970c1104e47c
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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