13826-86-3 → HCID 57158477, compound

HRID 912606Notes

Reaction equation

HRID 912606 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[N:3]=1.[B-](F)(F)(F)F.[N:22]([OH:24])=[O:23]>C(#N)C>[N+:22]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[NH:8][C:4]1[N:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1)[C:13]#[N:14])([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 2629613826-86-3HCID 111955954-((4-Chloropyrimidin-2-yl)amino)benzonitrile

Product 1

HCID 57158477HCID 57158477, compoundYield 129.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile (0.005 mol) and nitryl tetrafluoroborate (0.0025 mol) in acetonitrile (5 ml) was stirred at room temperature for 4 h. The material was quenched with saturated bicarbonate (50 ml) on cracked ice. The mixture was allowed to reach room temperature, and the yellow solid was filtered off. The solid was adsorbed onto silica and purified by column chromatography (eluent: 30%, 50%, 60%, 70% CH2Cl2 in hexanes). The solvent of the desired fraction was evaporated and the residue was dried, yielding 0.89 g (64%) of 3-nitro-4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile. (interm. 51)

Workup

  1. customThe material was quenched with saturated bicarbonate (50 ml)
  2. customto reach room temperature
  3. filtrationthe yellow solid was filtered off
  4. custompurified by column chromatography (eluent: 30%, 50%, 60%, 70% CH2Cl2 in hexanes)
  5. customThe solvent of the desired fraction was evaporated
  6. customthe residue was dried

Sources & evidence

ORD record
ord-77cada181aa747e4967730c11f205d1e
Source dataset
uspto-grants-2011_09
Patent number
US08026248B2

Reaction notes

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