2-Aminopyridine → HCID 68428971, compound

HRID 81681Notes

Reaction equation

HRID 81681 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](CC([O-])=O)[CH:17]=2)[N:12]=[CH:11][N:10]=1.C(=O)([O-])[O-:24].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:24])[CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 104392-AminopyridineHCID 10796Cesium carbonateHCID 866459052-(4-Chloroquinazolin-6-yl)acetate

Product 1

HCID 68428971HCID 68428971, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of pyridin-2-amine (101 mg, 1.08 mmol) and 4-chloroquinazolin-6-ylacetate (200 mg, 0.90 mmol) in toluene (4 ml), tris(dibenzylideneacetone)dipalladium (0) (82.0 mg, 0.090 mmol), (±)BINAP (112.0 mg, 0.180 mmol) and cesium carbonate (585 mg, 1.80 mmol) were added, and the mixture was stirred under nitrogen atmosphere at 120° C. for 2 hours. The reaction liquid was filtered, followed by vacuum concentration of the filtrate. The residue was suspended in water and then extracted with chloroform, and thereafter the combined organic layers were washed with water and a saturated saline solution and dried over anhydrous sodium sulfate, followed by being concentrated under reduced pressure. The resultant residue was dissolved in ammonia water (1 ml) and methanol (4 ml), and the solution was stirred at 50° C. for 2 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure, the resultant residue was suspended in ether, and the precipitate was obtained through filtration, washed with ether and then dried to give 4-(pyridin-2-ylamino)quinazolin-6-ol (138 mg, yield: 64%) as a brown solid.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. extractionextracted with chloroform
  4. washthe combined organic layers were washed with water
  5. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  6. concentrationby being concentrated under reduced pressure
  7. dissolutionThe resultant residue was dissolved in ammonia water (1 ml)
  8. stirringmethanol (4 ml), and the solution was stirred at 50° C. for 2 hours
  9. temperatureThe reaction solution was cooled to room temperature
  10. concentrationconcentrated under reduced pressure
  11. customthe precipitate was obtained through filtration
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-3d901db4a2d94b1cb0b910ff3494ed07
Source dataset
uspto-grants-2014_09
Patent number
US08846700B2

Reaction notes

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