Hydrochloric Acid → 4-[[5-Bromo-4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile

HRID 1363901Notes

Reaction equation

HRID 1363901 reaction equation
[Br:1][C:2]1[C:3]([NH:18][C:19]2[CH:26]=[CH:25][C:22]([C:23]#N)=[CH:21]C=2)=[N:4][C:5](NC2C(C)=CC(C)=CC=2C)=[N:6][CH:7]=1.CCO[CH2:30][CH3:31].Cl.[NH2:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=1.O1CCOC[CH2:43]1>>[Br:1][C:2]1[C:3]([NH:18][C:19]2[C:26]([CH3:43])=[CH:25][C:22]([CH3:23])=[CH:21][C:30]=2[CH3:31])=[N:4][C:5]([NH:33][C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)=[N:6][CH:7]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 133964-AminobenzonitrileHCID 312751,4-DioxaneHCID 221700964-[[5-Bromo-2-[(2,4,6-trimethylphenyl)amino]4-pyrimidinyl]amino]benzonitrile

Product 1

HCID 4863834-[[5-Bromo-4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrileYield 13%

Procedure

To a flask containing intermediate 2 (0.00285 mol) was added ether. To this homogeneous solution was added HCl in diethyl ether (1M; 0.00855 mol). The solvent was evaporated and 1,4-dioxane (20 ml) was added. Finally, 4-aminobenzonitrile (0.00291 mol) and 1,4-dioxane (15 ml) were added and the reaction mixture was stirred and refluxed for seven days. The solvent was evaporated, the residue dissolved in CH2Cl2, washed with 1 M NaOH, and the solvent evaporated. The residue was dissolved in CH2Cl2 (10 ml) and the precipitate was filtered off and dried, yielding 0.15 g (13%) of 4-[[5-bromo-4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile (comp. 3).

Workup

  1. customThe solvent was evaporated
  2. addition1,4-dioxane (20 ml) was added
  3. temperaturerefluxed for seven days
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in CH2Cl2
  6. washwashed with 1 M NaOH
  7. customthe solvent evaporated
  8. dissolutionThe residue was dissolved in CH2Cl2 (10 ml)
  9. filtrationthe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-52d46be9e27f4794a492e9ea7081e43c
Source dataset
uspto-grants-2011_02
Patent number
US07887845B2

Reaction notes

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