2-Aminopyridine → HCID 22326898, compound

HRID 495479Notes

Reaction equation

HRID 495479 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CCN(C(C)C)C(C)C>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 22326898HCID 22326898, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

To a N2 purged sealed tube, 2,4-dichloropyrimidine (1.0 g, 6.7 mmol, 1.2 eq.) and 2-aminopyridine (0.53 g, 5.6 mmol, 1.0 eq.) were added followed by 7 mL of anhydrous IPA. To the resulting suspension DIEA (0.98 mL, 5.6 mmol, 1.0 eq.) was added. The reaction was heated to 90-100° C. and stirred for 12 h. The reaction mixture was cooled to RT and the solvent was removed. The crude mixture was further purified by column chromatography (0-20% EtOAc in hexanes) providing pure (2-chloro-pyrimidin-4-yl)-pyridin-2-yl-amine.

Workup

  1. customTo a N2 purged
  2. customsealed tube
  3. temperatureThe reaction mixture was cooled to RT
  4. customthe solvent was removed
  5. customThe crude mixture was further purified by column chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-21d7dbebdc4047408d3969bd7ff2f4e9
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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