Methanol → HCID 19690690, compound

HRID 1463245Notes

Reaction equation

HRID 1463245 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:15][C:16]#[CH:17])[C:5](=[O:18])[C:4]=1[CH3:19])[CH3:2].[CH3:20][O-:21].[Na+].CI.[CH3:25][OH:26]>>[CH3:20][O:21][C:16]([O:26][CH3:25])([CH3:17])[CH2:15][N:6]1[C:5](=[O:18])[C:4]([CH3:19])=[C:3]([CH2:1][CH3:2])[N:8]=[C:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 19690703HCID 19690703, compound2×

Product 1

HCID 19690690HCID 19690690, compound

Procedure

To a stirred suspension of 4.51 g (17.9 mmol) of 6-ethyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 5) in 30 mL of methanol was added 7.50 g (34.7 mmol) of a 25% by weight solution of sodium methoxide in methanol. The mixture was warmed until homogeneous and 2.2 mL (35.3 mmol) of methyl iodide was added. The mixture was refluxed for 4 h and then rotovapped to remove the bulk of the methanol. The residue was partitioned between 100 mL of water and two 100 mL portions of ether. The combined ether layers were washed with 50 mL of brine and dried over MgSO4. Removal of the solvent afforded 4.35 g of a yellow oil. Flash chromatography on a column of 50 g of silica gel, eluting with 20, 30, 40 and 50% ether in hexanes furnished 3.30 g (58%) of 3-(2,2-dimethoxypropyl)-6-ethyl-5-methyl-2-phenyl- 4(3H)-pyrimidinone (compound 36), mp 80°-83° C. 1H-NMR (CDCl3) δ1.15(3H,s), 1.25(3H,t), 2.15(3H,s), 2.65(2H,q), 2.85(6H,s), 4.4(2H,m), 7.45(5H,s).

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 4 h
  3. customto remove the bulk of the methanol
  4. customThe residue was partitioned between 100 mL of water and two 100 mL portions of ether
  5. washThe combined ether layers were washed with 50 mL of brine
  6. dry with materialdried over MgSO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-eb37586cb9fb4f7d917b2d31d671082e
Source dataset
uspto-grants-1994_04
Patent number
US05300477

Reaction notes

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