Propanedioic acid, monoethyl ester → 7'-Hydroxyspiro[cyclopentane-1,2'-imidazo[1,2-a]pyrimidin]-5'-one

HRID 2408339Notes

Reaction equation

HRID 2408339 reaction equation
[Na].[NH:2]1[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][N:4]=[C:3]1[NH2:11].[C:12](OCC)(=[O:17])[CH2:13][C:14]([O-])=[O:15]>CO.CCOCC>[OH:17][C:12]1[N:11]=[C:3]2[NH:2][C:6]3([CH2:10][CH2:9][CH2:8][CH2:7]3)[CH2:5][N:4]2[C:14](=[O:15])[CH:13]=1

Participants

6

Reactant 3

HCID 3595298Propanedioic acid, monoethyl esterHCID 5360545SodiumHCID 68034535HCID 68034535, compound

Product 1

HCID 1360696037'-Hydroxyspiro[cyclopentane-1,2'-imidazo[1,2-a]pyrimidin]-5'-oneYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

2.37 g of sodium are added in a fractionated way to 10 mL of MeOH. After total dissolution, 5.68 g of 1,3-diazaspiro[4.4]non-2-en-2-amine solubilized beforehand in 5 mL of MeOH, and then 25.38 mL of ethyl malonate are added. The mixture is heated to 100° C., after 4 h of heating, the medium is dry concentrated. The oil obtained is taken up in ether. The precipitate is filtered and the residue is then taken up in 10 mL of H2O and acidified with conc. HCl until pH 3-4. The formed precipitate is filtered, washed with ether and dried in the oven in vacuo. 3.97 g (yield=74%) of 7′-hydroxyspiro[cyclopentane-1,2′-imidazo[1,2-a]pyrimidin]-5′-one are obtained as a beige solid.

Workup

  1. temperatureof heating
  2. customthe medium is dry
  3. concentrationconcentrated
  4. customThe oil obtained
  5. filtrationThe precipitate is filtered
  6. filtrationThe formed precipitate is filtered
  7. washwashed with ether
  8. customdried in the oven in vacuo

Sources & evidence

ORD record
ord-9809c0c1320d498a91fa8845622f3f52
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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