Diethyl methylmalonate → HCID 178431759, compound

HRID 1060562Notes

Reaction equation

HRID 1060562 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)(=[NH:3])[NH2:2].[CH3:14][CH:15]([C:21](OCC)=[O:22])[C:16](OCC)=[O:17].C[O-].[Na+]>C(O)C>[O:9]1[C:8]2[CH:12]=[CH:13][C:5]([CH2:4][C:1]3[N:2]=[C:16]([OH:17])[C:15]([CH3:14])=[C:21]([OH:22])[N:3]=3)=[CH:6][C:7]=2[O:11][CH2:10]1

Participants

5

Reactant 3

HCID 11857Diethyl methylmalonateHCID 4995343HCID 4995343, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 178431759HCID 178431759, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (350 mL) was added 5-(amidino)methyl-1,3-benzodioxolane (50 g, 0.23 mol), diethyl methylmalonate (50 mL), and sodium methoxide (120 mL of 25 wt % in methanol). After refluxing for 5 hours, the solvent was removed in vacuo. The residue was dissolved in water, washed with ethyl acetate, treated with charcoal, and acidified with 6 N HCl. The resulting solid was collected by filtration, washed with water, CH3CN and ethyl ether to give 54 g of 2-[(1,3-benzodioxol-5-yl)methyl]-4,6-dihydroxy-5-methylpyrimidine.

Workup

  1. temperatureAfter refluxing for 5 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washwashed with ethyl acetate
  5. additiontreated with charcoal
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water, CH3CN and ethyl ether

Sources & evidence

ORD record
ord-ebd75cbdcbdf49b9b55bf97944ac028d
Source dataset
uspto-grants-2003_02
Patent number
US06525051B2

Reaction notes

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