Propanedioic acid, monoethyl ester → 2-hydroxy-7,7-dimethyl-1H,4H,6H,7H,8H-[1,3]diazino[1,2-a]pyrimidin-4-one

HRID 2408358Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

1.4 g of sodium are added in a fractionated way to 15 mL of MeOH. After total dissolution, 2.7 g of 5,5-dimethyl-1,4,5,6-tetrahydropyrimidin-2-amine solubilized beforehand in 5 mL of MeOH, and then 16.5 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 conc. HCl up to pH 3-4. The precipitate formed is filtered, washed with ether and dried in the oven in vacuo. 2 g (yield=72%) of 2-hydroxy-7,7-dimethyl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are obtained as a beige solid used as such.

Workup

temperatureof heating
customthe medium is dry
concentrationconcentrated
filtrationThe precipitate is filtered
customThe precipitate formed
filtrationis filtered
washwashed with ether
customdried in the oven in vacuo

Sources & evidence

ORD record: ord-e610790dc65e4d9e9be6b9e678e2cbd2
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815853B2

Reaction notes

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