Urea → 2,2-Dimethyl-1,3-dioxane-4,6-dione

HRID 2185014Notes

Reaction equation

HRID 2185014 reaction equation
N[C:2](N)=O.Cl[CH:6]([C:11]([O-:13])=[O:12])[C:7]([O:9]C)=[O:8].C(N([CH2:19][CH3:20])CC)C>CN(C=O)C>[CH3:2][C:19]1([CH3:20])[O:13][C:11](=[O:12])[CH2:6][C:7](=[O:8])[O:9]1

Participants

5

Reactant 3

HCID 1176UreaHCID 8471TriethylamineHCID 86762096Methyl chloromalonate

Product 1

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

About 200 mg of (4) are swollen in solvent in the cold (e.g. at 0° C. in DMF) and treated with about 1 mmol of monomethyl chloromalonate. About 0.5 ml of triethylamine is added and the mixture is stirred for about 2 h at 0° C. and for 1 h at a low heat (e.g. 50° C.). After washing the resin (3) is isolated. The free derivative of the N,N′-dialkylbarbituric acid (3, Li-P=H) is then obtained by removal of the linker.

Workup

  1. temperaturea low heat (e.g. 50° C.)
  2. washAfter washing the resin (3)
  3. customis isolated

Sources & evidence

ORD record
ord-a2f9dfa15e6b4eb28d4259802a6230a4
Source dataset
uspto-grants-2002_06
Patent number
US06399653B1

Reaction notes

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