Ethanol → 5,6-Diamino-2-(ethoxymethyl)-4(3H)-pyrimidinone hemimaleate

HRID 326875Notes

Reaction equation

HRID 326875 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5]([CH2:9][O:10][CH2:11][CH3:12])=[N:6][C:7]=1[NH2:8].[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]\[C:17]([OH:19])=[O:18].C(O)C>CO>[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]\[C:17]([OH:19])=[O:18].[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5]([CH2:9][O:10][CH2:11][CH3:12])=[N:6][C:7]=1[NH2:8].[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5]([CH2:9][O:10][CH2:11][CH3:12])=[N:6][C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 444266Maleic AcidHCID 1357498055,6-diamino-2-(ethoxymethyl)-4(3H)-pyrimidinone

Product 1

HCID 1372254875,6-Diamino-2-(ethoxymethyl)-4(3H)-pyrimidinone hemimaleate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.4 g (0.0185 mole) of 5,6-diamino-2-(ethoxymethyl)-4(3H)-pyrimidinone, 4.4 g (0.0379 mole) of maleic acid, 300 ml of absolute ethanol and 100 ml of methanol is brought to reflux. The small insoluble portion is removed by filtration while hot. After cooling, the precipitate formed is isolated by filtration; it is washed with ethyl ether and recrystallized from absolute ethanol. Yld: 2.0 g (45%), m.p. 192°-194° C.

Workup

  1. temperatureto reflux
  2. customThe small insoluble portion is removed by filtration while hot
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. customis isolated by filtration
  6. washit is washed with ethyl ether
  7. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-cadf393addc9402e81e20922153fe8b6
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Reaction notes

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