3-Aminopyridine → HCID 9980614, compound

HRID 30441Notes

Reaction equation

HRID 30441 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].FC(S(O[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)[N:18]=[C:17]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[N:16]=1)(=O)=O)(F)F.[NH2:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:35]1([C:17]2[N:16]=[C:15]([NH:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:22]=3)[N:18]=2)[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1

Participants

6

Reactant 3

HCID 100093-AminopyridineHCID 10796Cesium carbonateHCID 597896832-Morpholin-4-yl-6-[3-(phenylmethoxy)phenyl]pyrimidin-4-yl (trifluoromethyl)sulfonate

Product 1

HCID 9980614HCID 9980614, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask, oven dried and kept under N2 atmosphere was charged with Cs2CO3 (1.4 eq), Pd(OAc)2 (5 mol %), and S-(−)-BINAP (1.5×mol of Pd catalyst). The flask was purged with N2 for about 5-10 min and a solution of 2-morpholin-4-yl-6-[3-(phenylmethoxy)phenyl]pyrimidin-4-yl (trifluoromethyl) sulfonate (1eq) in dry THF (20 mL) was added via a syringe, followed by 3-aminopyridine (2 eq,) in one portion. The flask was equipped with a reflux condenser, purged again with N2 for 5 min and the reaction mixture was refluxed overnight. An efficient stirring is very important. The reaction mixture was cooled down to room temperature and the solvent was evaporated under reduced pressure. The residue was washed with water (x2) and triturated with methanol to afford the desired {2-morpholin-4-yl-6-[3-(phenylmethoxy)phenyl]pyrimidin-4-yl}-3-pyridylamine.

Workup

  1. customA round bottom flask, oven dried
  2. customThe flask was purged with N2 for about 5-10 min
  3. customThe flask was equipped with a reflux condenser
  4. custompurged again with N2 for 5 min
  5. temperaturethe reaction mixture was refluxed overnight
  6. customthe solvent was evaporated under reduced pressure
  7. washThe residue was washed with water (x2)
  8. customtriturated with methanol

Sources & evidence

ORD record
ord-a6566fe5437b4a4983245283bfc839d4
Source dataset
uspto-grants-2008_09
Patent number
US07423148B2

Reaction notes

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