Methyl iodide → HCID 57445390, compound

HRID 1993340Notes

Reaction equation

HRID 1993340 reaction equation
[C:1]([O-:4])([O-])=O.[Cs+].[Cs+].[CH2:7]([C:14]1[NH:19][C:18](=O)[CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CI>CN(C=O)C.C1COCC1>[CH2:7]([C:14]1[N:19]([CH3:18])[C:1](=[O:4])[CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 436545842-benzylpyrimidin-4(3H)-one

Product 1

HCID 57445390HCID 57445390, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cs2CO3 (24.6 g, 75.7 mmol) was added to 2-benzyl-3H-pyrimidin-4-one (Step 1, 12.8 g) in DMF (80 mL) and THF (60 mL) at 0° C. After 10 min, MeI (4.3 mL, 68.8 mmol) was added, and the reaction was warmed to RT. After 3 h, the reaction was decanted, diluted with CH2Cl2, and washed with H2O, and aq. sat. NaCl solution. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Et2O and Hexane (1:1) were added and the solvent was evaporated to provide a brown solid. The solid was triturated with 30′ EtOAc/hexane to afford the title compound as a light brown solid. The filtrate was purified by chromatography with 0-5% MeOH/CHCl3 to afford additional compound. MS (ESI pos. ion) m/z: 201.0. (M+H). Calc'd for C12H12N2O: 200.09.

Workup

  1. waitAfter 3 h
  2. customthe reaction was decanted
  3. additiondiluted with CH2Cl2
  4. washwashed with H2O, and aq. sat. NaCl solution
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. additionEt2O and Hexane (1:1) were added
  8. customthe solvent was evaporated
  9. customto provide a brown solid
  10. customThe solid was triturated with 30′ EtOAc/hexane

Sources & evidence

ORD record
ord-52f23a1ca5e843e9bc2f695d296ebcf4
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

Loading…