Methyl iodide → HCID 15485642, compound

HRID 367264Notes

Reaction equation

HRID 367264 reaction equation
[CH2:1]([N:5]1[C:10]([CH3:11])=[CH:9][C:8](=[O:12])[NH:7][C:6]1=[O:13])[CH2:2][CH2:3][CH3:4].[C:14]([O-])([O-])=O.[K+].[K+].CI.C(Cl)Cl.CCOC(C)=O>CN(C=O)C>[CH2:1]([N:5]1[C:10]([CH3:11])=[CH:9][C:8](=[O:12])[N:7]([CH3:14])[C:6]1=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12703038HCID 12703038, compoundHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 15485642HCID 15485642, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To 2.3 g (12.62 mmol) of 1-butyl-6-methyl-1H-pyrimidine-2,4-dione in 100 mL DMF was added 3.49 (25.2 mmol) of K2CO3, 0.98 mL (2.24 g, 15.76 mmol) of MeI and the reaction mixture was heated to 65° C. After 16.5 h, TLC (8/1 CH2Cl2 /EtOAc) indicated the consumption of starting material (Rf =0.15). After cooling to 23° C., the resulting slurry was filtered through Celite, and evaporated to a yellow. This oil was dissolved in 100 mL EtOAc, extracted with 100 mL brine, 3×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered and evaporated to a yellow oil. Flash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (20/1 to 4/1), gave 2.03 g (10.34 mmol, an 82% yield) of the title compound as a white crystalline solid. mp: 181-182° C.; 1H NMR (300 MHz, CDCl3): δ 0.95 (t, J=7.3 Hz, 3H), 1.38 (hex, J=7.3 Hz, 2H), 1.57-1.67 (m, 2H), 2.25 (s, 3H), 3.32 (s, 3H), 3.81 (t, J=7.4 Hz, 2H), 5.59 (s, 1H); IR (KBr, cm-1): 3083w, 2955w, 2876w, 1702s, 1665s, 1614s, 1446s, 1435s, 1368w, 1043w; MS (ES) m/z (relative intensity): 197 (M+ +H, 100). Anal. Calcd. for C10H16N2O2 : C, 61.20; H, 8.22; N, 14.27. Found: C, 60.95; H, 8.19; N, 14.16.

Workup

  1. customthe consumption of starting material (Rf =0.15)
  2. temperatureAfter cooling to 23° C.
  3. filtrationthe resulting slurry was filtered through Celite
  4. customevaporated to a yellow
  5. dissolutionThis oil was dissolved in 100 mL EtOAc
  6. extractionextracted with 100 mL brine, 3×100 mL H2O, 1×100 mL brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to a yellow oil
  10. washFlash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (20/1 to 4/1)
  11. customgave 2.03 g (10.34 mmol

Sources & evidence

ORD record
ord-13801b89b3d2460891014bfec97d50bc
Source dataset
uspto-grants-2000_10
Patent number
US06133273

Reaction notes

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