Ethanol → Sodium

HRID 528434Notes

Reaction equation

HRID 528434 reaction equation
[Na:1].[NH2:2][C:3]([NH2:5])=[O:4].[C:6]([O:12]COC)(=O)[CH2:7][C:8]([O-:10])=O.[CH2:16]([OH:18])C>>[OH:10][C:8]1[NH:5][C:3](=[O:4])[NH:2][C:6](=[O:12])[C:7]=1[O:18][CH3:16].[Na:1]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 1176UreaHCID 5360545SodiumHCID 21912471Methoxymethyl malonate

Product 2

HCID 5360545SodiumHCID 673031125-Methoxypyrimidine-2,4,6-triol

Conditions

Temperature
100 °C

Procedure

Under an atmosphere of nitrogen, sodium metal (1.15 g, 0.05 moles) was added portionwise to ethanol (dried over 4 Å molecular sieves, 50 mL) at 40° C. and the mixture stirred until a solution was formed. Urea (3.0 g, 0.05 moles) was added and the mixture heated at 100° C. for 15 minutes until complete dissolution was achieved. The reaction mixture was allowed to cool slightly and methoxymethyl malonate (8.1 g, 0.05 moles) added, a pink/white precipitate forming almost immediately. Further dry ethanol (10 mL) was added to maintain a stirrable mixture. The resultant suspension was heated at 100° C. (reflux) for 4 hours. The reaction mixture was concentrated in vacuo and the residue dried under high vacuum to give 6-Hydroxy-5-methoxy-1H-pyrimidine-2,4-dione, sodium salt as a pink/white solid, used in the subsequent step without analysis or purification.

Workup

  1. customwas formed
  2. temperatureto cool slightly
  3. customa pink/white precipitate forming almost immediately
  4. temperatureto maintain a stirrable mixture
  5. temperature(reflux) for 4 hours
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-55f28b00302049b0820ee59328fdc8c4
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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