Diethyl chlorophosphate → HCID 14460515, compound

HRID 1199650Notes

Reaction equation

HRID 1199650 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=O.[H-].[Na+].CCOP(Cl)(OCC)=O.[CH2:25]([C:27]1[O:31][N:30]=[C:29]([CH2:32][N+:33]#[C-:34])[N:28]=1)[CH3:26]>CN(C=O)C>[CH2:25]([C:27]1[O:31][N:30]=[C:29]([C:32]2[N:33]=[CH:34][N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:11](=[O:12])[N:2]([CH3:1])[C:3]=23)[N:28]=1)[CH3:26]

Participants

6

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 3443853-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dioneHCID 10654277HCID 10654277, compound

Product 1

HCID 14460515HCID 14460515, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-methyl-1,2,3,4-tetrahydro-2,4-dioxo-quinazoline (5 mmol) was dissolved in dry dimethyl formamide DMF (20 ml) and charged with sodium hydride (6 mmol). The resulting solution was cooled under N2 to -20° C., whereafter chlorodiethylphosphate (6 mmol) was added. The reaction mixture was kept under N2 with stirring and was allowed to reach room temperature and was then charged with a -30° C. cold solution of 5-ethyl-3-isocyanomethyl-1,2,4-oxadiazole(6 mmol) and K-t-butylate (6 mmol) in dry DMF (15 ml). The resulting mixture was stirred at room temperature for one hour whereafter the reaction mixture was evaporated in vacuo. The residue was partitioned between ethyl acetate and 4M sodium hydroxide. The organic phase was dried and evaporated. Yield 120 mg of title compound. M.p. 199.4°-202.2° C.

Workup

  1. additionwas added
  2. customto reach room temperature
  3. stirringThe resulting mixture was stirred at room temperature for one hour whereafter the reaction mixture
  4. customwas evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate and 4M sodium hydroxide
  6. customThe organic phase was dried
  7. customevaporated

Sources & evidence

ORD record
ord-59d76e002e4e45dfafee2a9b1d73f5fa
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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