2-Amino-5-(trifluoromethyl)pyridine → (7-Bromo-quinazolin-4-yl)-(5-trifluoromethyl-pyridin-2-yl)-amine

HRID 968568Notes

Reaction equation

HRID 968568 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][N:15]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 167808557-Bromo-4-chloroquinazoline

Product 1

HCID 11485491(7-Bromo-quinazolin-4-yl)-(5-trifluoromethyl-pyridin-2-yl)-amine

Procedure

Heat a mixture of 7-bromo-4-chloro-quinazoline (200 mg, 0.821 mmol) and 2-amino-5-trifluoromethyl-pyridine (239 mg, 1.48 mmol) at 230° C. for 2 minutes. Cool and partition the solid residue between EtOAc and 10% NaOH. Dry the EtOAc layer (Na2SO4), remove the solvent under reduced pressure, and purify via flash chromatography to yield (7-bromo-quinazolin-4-yl)-(5-trifluoromethyl-pyridin-2-yl)-amine as a yellow solid.

Workup

  1. temperatureHeat
  2. temperatureCool
  3. custompartition the solid residue between EtOAc and 10% NaOH
  4. dry with materialDry the EtOAc layer (Na2SO4)
  5. customremove the solvent under reduced pressure
  6. custompurify via flash chromatography

Sources & evidence

ORD record
ord-e3ef13ca0e6641ccaa6d0fb61940f61e
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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