Propanedioic acid, monoethyl ester → 7-hydroxy-2,2-dimethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

HRID 2408337Notes

Reaction equation

HRID 2408337 reaction equation
[Na].[Br-].[CH3:3][C:4]1([CH3:10])[NH:8][C:7]([NH2:9])=[N:6][CH2:5]1.[C:11](OCC)(=[O:16])[CH2:12][C:13]([O-])=[O:14]>CO>[OH:16][C:11]1[N:9]=[C:7]2[NH:8][C:4]([CH3:10])([CH3:3])[CH2:5][N:6]2[C:13](=[O:14])[CH:12]=1

Participants

5

Reactant 3

HCID 3595298Propanedioic acid, monoethyl esterHCID 5360545SodiumHCID 86700698HCID 86700698, compound

Product 1

HCID 1362693147-hydroxy-2,2-dimethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-oneYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 250 mL of methanol under nitrogen, 5.21 g of sodium are added. Once dissolution is total and after returning to RT, 20 g of 5,5-dimethyl-4,5-dihydro-imidazol-2-amine bromide and 31.2 g of ethyl malonate are added. The medium is heated with reflux for 16 h. The reaction medium is dry concentrated, and then taken up in 40 mL of ice water. The expected product is precipitated by adding 1N HCl. The obtained precipitate is filtered, washed with water and then dried in the oven at 50° C. 18.62 g (yield=97%) of 7-hydroxy-2,2-dimethyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one are obtained as a white solid.

Workup

  1. dissolutionOnce dissolution
  2. customafter returning to RT
  3. temperatureThe medium is heated
  4. temperaturewith reflux for 16 h
  5. customThe reaction medium is dry
  6. concentrationconcentrated
  7. customThe expected product is precipitated
  8. additionby adding 1N HCl
  9. filtrationThe obtained precipitate is filtered
  10. washwashed with water
  11. customdried in the oven at 50° C

Sources & evidence

ORD record
ord-de848eb8ff8a4d6bb01efd1f986e3ea4
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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