Triphosgene → 7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271407Notes

Reaction equation

HRID 271407 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[C:24]([NH:26][NH2:27])[N:23]=[CH:22][N:21]=2)=[CH:16][CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[CH:22][N:23]3[C:2](=[O:4])[NH:27][N:26]=[C:24]3[CH:25]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 587728354-(4-Chlorophenyl)-6-hydrazinylpyrimidine

Product 1

HCID 587728447-(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-oneYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of triphosgene (2.86 g, 9.66 mmol) in THF (10 mL) at room temperature under argon was added a suspension of 4-(4-chlorophenyl)-6-hydrazinylpyrimidine (825 mg, 3.22 mmol) in THF (10 mL). The reaction mixture was stirred overnight. Analysis by HPLC/MS indicated that no starting material remained. Solvent was removed under reduced pressure and water (50 mL) was added. After stirring for 30 min, the solid precipitate was collected and further washed with water (3×10 mL), then methanol (3×5 mL). The title compound (793 mg) was obtained as an off-white solid. HPLC/MS: retention time=2.74 min, [M+H]30 =247.

Workup

  1. customSolvent was removed under reduced pressure and water (50 mL)
  2. additionwas added
  3. stirringAfter stirring for 30 min
  4. customthe solid precipitate was collected
  5. washfurther washed with water (3×10 mL)

Sources & evidence

ORD record
ord-7eaeebd6b8bf45799d81b60bb33f17e7
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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