Water → 5-Pyrimidin-2-yl-1',2',3',6'-tetrahydro-[2,4']bipyridinyl

HRID 1038092Notes

Reaction equation

HRID 1038092 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:20][CH:19]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:23][N:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.O.[OH-].[Na+]>C(Cl)Cl>[N:28]1[CH:29]=[CH:30][CH:31]=[N:32][C:27]=1[C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH:17]=2)=[N:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 589464631,1-Dimethylethyl 3',6'-dihydro-5-(2-pyrimidinyl)[2,4'-bipyridine]-1'(2'h)-carboxylate

Product 1

HCID 589464495-Pyrimidin-2-yl-1',2',3',6'-tetrahydro-[2,4']bipyridinylYield 116.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Added 4M HCl/dioxane (5 ml) to solution of 5-Pyrimidin-2-yl-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (2Q) (110 mg, 0.325 mmol) in MeCl2 (5 ml) at room temperature, then stirred 4 hours. Evaporated solvent. Added MeCl2 (100 ml), H2O (50 ml) and 10% NaOH (3 ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding 3Q as a white solid (90 mg, 100%) ESMS (MH, 239) LCMS (MH, 239) Retention time=1.53 minutes.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customsolvent evaporated

Sources & evidence

ORD record
ord-539dd85ca07d474ca428259cc9e0c23d
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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