4-Amino-1,2,4-triazole → 2-phenyl-N-(1,2,4-triazol-4-yl)pyrimidine-5-carboxamide

HRID 2381951Notes

Reaction equation

HRID 2381951 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:37][N:38]1[CH:42]=[N:41][N:40]=[CH:39]1>C(Cl)Cl>[N:41]1[N:40]=[CH:39][N:38]([NH:37][C:13]([C:10]2[CH:11]=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][CH:9]=2)=[O:15])[CH:42]=1

Participants

6

Reactant 4

HCID 114324-Amino-1,2,4-triazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7473892-Phenylpyrimidine-5-carboxylic acid

Product 1

HCID 592000582-phenyl-N-(1,2,4-triazol-4-yl)pyrimidine-5-carboxamideYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenyl-pyrimidine-5-carboxylic acid (300 mg, 1.5 mmol) in DCM (10 mL) is added 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide (316 mg, 1.65 mmol) and N-hydroxybenzotriazole (223 mg, 1.65 mmol) at rt and the mixture is stirred for 10 min. 4-Amino-4H-1,2,4-triazole (252 mg, 3 mmol) is added and the mixture is stirred at rt for 3 days. The resulting precipitate is filtered, washed with DCM and water, and dried in vacuum oven at 40° C. overnight to afford 2-phenyl-pyrimidine-5-carboxylic acid [1,2,4]triazol-4-ylamide (270 mg) as a solid. MS: 267 (M+H); 1H NMR (300 MHz, DMSO): δ=7.59 (m, 3H), 8.50 (d, 2H), 8.84 (s, 2H), 9.36 (s, 2H). IC50=262.5 nM.

Workup

  1. stirringthe mixture is stirred at rt for 3 days
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with DCM and water
  4. customdried in vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-fccbda992dcc4dfc8e256051f25cc56c
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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