Propanedioic acid, monoethyl ester → HCID 136344290, compound

HRID 2408348Notes

Reaction equation

HRID 2408348 reaction equation
[Na].[CH3:2][C:3]1([CH3:10])[CH2:8][CH2:7][NH:6][C:5]([NH2:9])=[N:4]1.[C:11](OCC)(=[O:16])[CH2:12][C:13]([O-])=[O:14]>CO>[OH:16][C:11]1[N:9]=[C:5]2[NH:4][C:3]([CH3:10])([CH3:2])[CH2:8][CH2:7][N:6]2[C:13](=[O:14])[CH:12]=1

Participants

5

Reactant 3

HCID 3595298Propanedioic acid, monoethyl esterHCID 5360545SodiumHCID 178426522HCID 178426522, compound

Product 1

HCID 136344290HCID 136344290, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

1.2 g of sodium are added in a fractionated way to 15 mL of MeOH. After total dissolution, 3 g of 4,4-dimethyl-1,4,5,6-tetrahydropyrimidin-2-amine solubilized beforehand in 5 mL of MeOH are added, and then 14.4 mL of ethyl malonate. 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 conc.HCl down to pH 3-4. The formed precipitate is filtered, washed with ether and dried in the oven in vacuo. 1.14 g (yield=90%) of 2-hydroxy-8,8-dimethyl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are obtained as a beige solid used as such.

Workup

  1. additionare added
  2. temperatureof heating
  3. customthe medium is dry
  4. concentrationconcentrated
  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-dfb5d59ee9944e2fac27abefb7829eeb
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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