Pyrimidine-5-carboxaldehyde → N*3*-(3,5-Dichloro-phenyl)-N*5*-pyrimidin-5-ylmethyl-1H-[1,2,4]triazole-3,5-diamine

HRID 1486595Notes

Reaction equation

HRID 1486595 reaction equation
[N:1]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3][CH:2]=1.[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[N:22]=[C:21]([NH2:23])[NH:20][N:19]=2)[CH:13]=[C:14]([Cl:16])[CH:15]=1.ClC1C=C(N=C=S)C=C(Cl)C=1C#N>O>[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[N:22]=[C:21]([NH:23][CH2:7][C:5]3[CH:6]=[N:1][CH:2]=[N:3][CH:4]=3)[NH:20][N:19]=2)[CH:13]=[C:14]([Cl:16])[CH:15]=1

Participants

5

Reactant 3

HCID 2761034Pyrimidine-5-carboxaldehydeHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazoleHCID 867076002,6-Dichloro-4-isothiocyanatobenzonitrile

Product 1

HCID 178478187N*3*-(3,5-Dichloro-phenyl)-N*5*-pyrimidin-5-ylmethyl-1H-[1,2,4]triazole-3,5-diamineYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of pyrimidine-5-carbaldehyde (54 mg, 0.5 mmol) and N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (122 mg, 0.50 mmol) and picolineborane (54 mg, 0.5 mmol) was stirred at rt for 4 hours. The mixture was poured into water (20 mL) and extracted with EtOAc (3×10 mL). The extract was dried with sodium sulfate and the solvent was reduced to 2 mL. The remaining residue was loaded on a 25 g silica gel column and eluted with 5% MeOH in ethyl acetate to give 128 mg (76.2%) of desired product as a white solid. MS +m/z: 335.90 (M+H)+

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialThe extract was dried with sodium sulfate
  3. washeluted with 5% MeOH in ethyl acetate

Sources & evidence

ORD record
ord-53b6490892b747dd8b3f587d361a28de
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

Loading…