Hydrochloric Acid → HCID 488770, compound

HRID 1530875Notes

Reaction equation

HRID 1530875 reaction equation
Cl[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.[Br:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([Br:25])[C:19]=1[NH2:26].Cl>C(OCC)C.O1CCOCC1>[Br:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([Br:25])[C:19]=1[NH:26][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

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 814272,6-Dibromo-p-toluidineHCID 111955954-((4-Chloropyrimidin-2-yl)amino)benzonitrile

Product 1

HCID 488770HCID 488770, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile (0.003 mol), 2,6-dibromo-4-methyl-benzenamine (0.006 mol) and 1 M HCl in diethyl ether (4.5 ml) in 1,4-dioxane (10 ml) were combined in a tube and heated under Ar until all diethyl ether had evaporated. The tube was sealed and heated at 170° C. for 2.5 days. Silica gel was added, and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH:NH4OH 100:0:0 to 99:0.9:0.1). The desired fractions were collected and the solvent was evaporated. The residue was recrystallized from acetonitrile, filtered off and dried, yielding 0.22 g (15.9%) of 4-[[4-[(2,6-dibromo-4-methylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile (compound 61).

Workup

  1. customhad evaporated
  2. customThe tube was sealed
  3. additionSilica gel was added
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH:NH4OH 100:0:0 to 99:0.9:0.1)
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was recrystallized from acetonitrile
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-3a41ff65885541ceaacad31caa9cd8d5
Source dataset
uspto-grants-2001_03
Patent number
US06197779B1

Reaction notes

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