3-Aminopyridine → HCID 5329431, compound

HRID 968251Notes

Reaction equation

HRID 968251 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.CC([O-])(C)C.[Na+]>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:13]1([C:9]2[N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[N:7]=3)[CH:12]=[CH:11][N:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 100093-AminopyridineHCID 22288415HCID 22288415, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 5329431HCID 5329431, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (3-2, 50 mg, 0.2 mmol), 3-aminopyridine (22 mg, 0.23 mmol), NaOtBu (26 mg, 0.27 mmol), 2-biphenyl-di-tert-butylphosphine (5 mg, 0.02 mmol) was added Pd(OAc)2 (2 mg, 0.01 mmol) at room temperature. After 72 hours the mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 3-10% MeOH/CH2Cl2) gave the title compound as an off-white solid after trituration with Et2O/hexanes. 1H-NMR (500 MHz, CDCl3) δ 8.62 (d, J=1.95 Hz, 1H), 8.33 (d, J=5.37 Hz, 1H), 8.29 (d, J=4.40 Hz, 1H), 7.91 (d, J=7.08 Hz, 1H), 7.61 (d, J=1.22 Hz, 1H), 7.50 (m, 2H), 7.41 (m, 3H), 7.21 (m, 2H), 6.40 (d, J=5.37 Hz, 1H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-daa4650312724281bb38ef44904eb026
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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