Acetic Acid → HCID 22133754, compound

HRID 1826532Notes

Reaction equation

HRID 1826532 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[C:5]([NH2:17])=[C:4]([Cl:18])[N:3]=1.C(O)(=O)C.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O>CO>[NH2:1][C:2]1[N:7]=[C:6]2[C:5]([N:17]=[C:27]([C:26]3[CH:29]=[CH:30][CH:31]=[C:24]([F:23])[CH:25]=3)[N:8]2[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[C:4]([Cl:18])[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 680093-FluorobenzaldehydeHCID 22133823HCID 22133823, compound

Product 1

HCID 22133754HCID 22133754, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude crystals (3.2 g) of 3-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]benzonitrile were dissolved in 64 ml of methanol, then 3.2 ml of acetic acid and 1.7 ml of 3-fluorobenzaldehyde were added thereto and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated and was subjected to an azeotropy with toluene for two times. The resulting residue after concentration was dissolved in ethanol, a solution of 1.72 g of ferric chloride in 10 ml of ethanol was added and the mixture was heated under reflux for 1 hour. The reaction solution was returned to room temperature, concentrated to dryness and added to ice-water and the resulting crystals were collected by filtration to give 2.6 g of the title compound, i.e., 3-[2-amino-6-chloro-8-(3-fluorophenyl)-9H-9-purinyl]benzonitrile.

Workup

  1. concentrationThe reaction solution was concentrated
  2. concentrationThe resulting residue after concentration
  3. dissolutionwas dissolved in ethanol
  4. additiona solution of 1.72 g of ferric chloride in 10 ml of ethanol was added
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 1 hour
  7. customwas returned to room temperature
  8. concentrationconcentrated to dryness
  9. additionadded to ice-water
  10. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-34af4390eb204565b6fd623d02ff6759
Source dataset
uspto-grants-2006_05
Patent number
USRE039112E1

Reaction notes

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