Thymine → HCID 178430897, compound

HRID 1708514Notes

Reaction equation

HRID 1708514 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C(N(CC)CC)C.[NH:30]1[CH:38]=[C:36]([CH3:37])[C:34](=O)[NH:33][C:31]1=[O:32]>C(#N)C.CO>[CH3:37][C:36]1[C:38]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[N:30][C:31](=[O:32])[NH:33][CH:34]=1

Participants

7

Reactant 4

HCID 1135ThymineHCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 75654Diphenyl chlorophosphate

Product 1

HCID 178430897HCID 178430897, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

69 g (1 mol) of 1,2,4-triazole are suspended in 800 ml of dry acetonitrile under a protecting gas (argon). 251 g (0.95 mol) of diphenyl chlorophosphate are added to the suspension at 0°-10° C. Subsequently, in the course of 1 hour, 151.79 g (1.5 mol) of triethylamine are added dropwise before 63 g (0.5 mol) of thymine are added. The resulting suspension is stirred for 12 hours at room temperature. Finally, the mixture is heated for 5 hours at 60°-80° C. 40 ml of methanol are added to the cooled suspension and the mixture is stirred for 2 hours at room temperature. The suspension is filtered; the residue is stirred with one liter of diisopropyl ether, filtered off again by suction and stirred with 800 ml of water. The aqueous suspension is filtered and the solid residue is recrystallized from 1300 ml of dimethylformamide. 28.6 g of 5-methyl-4-(1,2,4 -triazol-1-yl)pyrimdin-2(1H)-one are obtained with melting point 275°-280° C.

Workup

  1. additionare added
  2. temperatureFinally, the mixture is heated for 5 hours at 60°-80° C
  3. stirringthe mixture is stirred for 2 hours at room temperature
  4. filtrationThe suspension is filtered
  5. stirringthe residue is stirred with one liter of diisopropyl ether
  6. filtrationfiltered off again by suction
  7. stirringstirred with 800 ml of water
  8. filtrationThe aqueous suspension is filtered
  9. customthe solid residue is recrystallized from 1300 ml of dimethylformamide

Sources & evidence

ORD record
ord-96ec81c771054dfe92db7d8e28b63041
Source dataset
uspto-grants-1994_10
Patent number
US05359067

Reaction notes

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