Phosphate → Dihydro-1-[3,5-dimethylphenyl]-1,2,4-triazine-3,5(2H,4H)dione

HRID 1493613Notes

Reaction equation

HRID 1493613 reaction equation
C[O-].[Na+].NC(N)=O.[NH2:8][C:9]([NH:11][N:12]([CH2:21][C:22]([O:24]C)=O)[C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)=[O:10].P([O-])([O-])([O-])=O>C(COC)OC.CCCCCC.CCOCC>[CH3:20][C:15]1[CH:14]=[C:13]([N:12]2[CH2:21][C:22](=[O:24])[NH:8][C:9](=[O:10])[NH:11]2)[CH:18]=[C:17]([CH3:19])[CH:16]=1

Participants

7

Reactant 4

HCID 1061PhosphateHCID 1176UreaHCID 10942334Sodium MethoxideHCID 53693452HCID 53693452, compound

Product 1

HCID 19829863Dihydro-1-[3,5-dimethylphenyl]-1,2,4-triazine-3,5(2H,4H)dioneYield 64%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 21584099Diethylether hexaneSolvent

Procedure

Sodium methoxide (0.32 g, 5.96 mmol) was added to a stirred solution of the urea (Intermediate 37; 0.75 g, 2.98 mmol) in dimethoxyethane (30 ml) over 4A sieves under a nitrogen atmosphere. After stirring at room temperature for ca. 30 min the resultant slurry was added to pH 6.5 aqueous phosphate buffer (50 ml) and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with saturated brine (50 ml), dried and evaporated to afford an orange solid. Trituration of this material with hexane/ether (1:1) (2×15 ml) gave the title compound as a light pink solid (0.52 g, 64%), m.p. ca 255° (dec.).

Workup

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. washThe combined extracts were washed with saturated brine (50 ml)
  3. customdried
  4. customevaporated
  5. customto afford an orange solid

Sources & evidence

ORD record
ord-1f8af137903c449184d531c206f9ae2f
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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