Propanedioic acid, monoethyl ester → HCID 136344295, compound

HRID 2408362Notes

Reaction equation

HRID 2408362 reaction equation
[Na].Br.[CH2:3]1[C:5]2([CH2:10][NH:9][C:8]([NH2:11])=[N:7][CH2:6]2)[CH2:4]1.[C:12](OCC)(=[O:17])[CH2:13][C:14]([O-])=[O:15]>CO>[OH:17][C:12]1[N:11]=[C:8]2[NH:9][CH2:10][C:5]3([CH2:4][CH2:3]3)[CH2:6][N:7]2[C:14](=[O:15])[CH:13]=1

Participants

5

Reactant 3

HCID 3595298Propanedioic acid, monoethyl esterHCID 5360545SodiumHCID 86700703HCID 86700703, compound

Product 1

HCID 136344295HCID 136344295, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

1.1 g of sodium are added in a fractionated way to 15 mL of MeOH. After total dissolution, 1.6 g of 5,7-diazaspiro[2.5]oct-5-en-6-amine hydrobromide solubilized beforehand in 5 mL of MeOH, and then 8 mL of ethyl malonate are added. The mixture is heated to 100° C., after 4 h of heating, the medium is dry concentrated. The obtained oil is taken up in ether. The precipitate is filtered and then the residue is taken up in 7 mL of H2O and acidified with concentrated HCl up to pH 3-4. The formed precipitate is filtered, washed with ether and dried in the oven in vacuo. 1.5 g (yield=60%) of 8′-hydroxy-1′,2′-dihydro-spiro[cyclopropane-1,3′-pyrimido[1,2-a]pyrimidin]-6′-one are obtained as a beige solid used as such.

Workup

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

Sources & evidence

ORD record
ord-377b78c3c2bd4e5486158cc71eae7103
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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