Methyl iodide → 1-Methyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

HRID 1681875Notes

Reaction equation

HRID 1681875 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:11][NH:10][CH:9]=[N:8][CH2:7]1)=[O:5].[H-].[Na+].[CH3:14]I>CN(C=O)C>[CH3:14][N:8]1[CH2:7][CH:6]([C:4]([O:3][CH3:2])=[O:5])[CH2:11][N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 199620591,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine Hydrochloride

Product 1

HCID 152943851-Methyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine hydrochloride (300 mg, 1.35 mmol) and NaH (60% in mineral oil 107 mg, 1.35 mmol) were suspended in anhydrous DMF (5 ml) in an oven dried round bottom flask with stirring under nitrogen. After stirring 15 minutes CH3I 84μl, 1.35 mmol) was added via syringe and stirring continued 3 hours at room temperature. The solvents were evaporated in vacuo and the residue triturated with chloroform. The resulting suspension was filtered and evaporated in vacuo. Chromatography (silica, chloroform/methanol, 9:1) gave 160 mg (76%) crystals mp 93°-95° C. identified by 300 MHz nmr; ms m/z=156.

Workup

  1. customdried round bottom flask
  2. additionwas added via syringe
  3. stirringstirring
  4. customThe solvents were evaporated in vacuo
  5. customthe residue triturated with chloroform
  6. filtrationThe resulting suspension was filtered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-7a3c6819f4264119b7aff823bfea863f
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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