Thymine → HCID 178430897, compound

HRID 1708513Notes

Reaction equation

HRID 1708513 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[CH:10]=[N:9][CH:8]=[N:7]1.C(N(CC)CC)C.[NH:18]1[CH:26]=[C:24]([CH3:25])[C:22](=O)[NH:21][C:19]1=[O:20]>C(#N)C.O>[CH3:25][C:24]1[C:26]([N:6]2[CH:10]=[N:9][CH:8]=[N:7]2)=[N:18][C:19](=[O:20])[NH:21][CH:22]=1

Participants

7

Reactant 4

HCID 1135ThymineHCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychloride

Product 1

HCID 178430897HCID 178430897, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

50.6 g (0.33 mol) of phosphoryl trichloride are added under a protecting gas (nitrogen) to a suspension of 69 g (1 mol) of 1,2,4-triazole in 800 ml of dry acetonitrile at an internal temperature of 0°-50° C. During a period of 1 hour, 101.2 g (1 mol) of triethylamine are then added dropwise. After stirring for a further 40 minutes at room temperature, 18.9 g (0.15 mol) of thymine are added. The suspension is stirred for 24 hours at room temperature, 25 ml of water are added and the mixture is stirred for a further 10 minutes and then filtered. The yellow residue is suspended in 400 ml of water, stirred and filtered off by suction after 1 hour. 1.72 g of 5-methyl-4-(1,2,4-triazol-1-yl)-pyrimidin-2-(1H)-one are obtained as a yellow powder with melting point 258°-264° C. The acetonitrile solution is concentrated, the residue is suspended in 400 ml of water, stirred and filtered off by suction. In this manner, a further 7.21 g of the compound are obtained. The title compound can be recrystallized from dimethylformamide and then melts at 275°-280° C. 1H NMR (60 MHz, d6 -DMSO), δ[ppm]: approx. 12.0 (s, broad, 1H), 9.33 (s, 1H), 8.40 (s, 1H), 8.13 (s, 1H), 2.3 (s, 3H).

Workup

  1. stirringThe suspension is stirred for 24 hours at room temperature
  2. stirringthe mixture is stirred for a further 10 minutes
  3. filtrationfiltered
  4. stirringstirred
  5. filtrationfiltered off by suction after 1 hour

Sources & evidence

ORD record
ord-b03f928881124f369ecd7a1a34ddf8ae
Source dataset
uspto-grants-1994_10
Patent number
US05359067

Reaction notes

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