Chloroacetyl chloride → 2-Chloro-1-(5-pyrimidin-2-yl-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-yl)-ethanone

HRID 1038093Notes

Reaction equation

HRID 1038093 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[N:6]1[CH:11]=[CH:10][CH:9]=[N:8][C:7]=1[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=2)=[N:16][CH:17]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([N:21]1[CH2:22][CH:23]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([C:7]3[N:6]=[CH:11][CH:10]=[CH:9][N:8]=3)=[CH:17][N:16]=2)[CH2:19][CH2:20]1)=[O:4]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 589464495-Pyrimidin-2-yl-1',2',3',6'-tetrahydro-[2,4']bipyridinyl

Product 1

HCID 589464642-Chloro-1-(5-pyrimidin-2-yl-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-yl)-ethanoneYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Added chloroacetyl chloride (0.35 g, 4.39 mmol) in MeCl2 (15 ml) to a solution of 5-Pyrimidin-2-yl-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl (3Q) (0.4 g, 1.68 mmol) and triethylamine (0.4 g, 2.87 mmol) in MeCl2 (10 ml) at 0° C., then stirred 2 hours at 0° C. Added saturated NaHCO3 solution and stirred an additional hour at 0° C. MeCl2 (100 ml) was added, organic layer separated, dried over Na2SO4, filtered and solvent evaporated yielding 4Q as a pale yellow solid (0.53 g, 100%) ESMS (MH 315).

Workup

  1. customorganic layer separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customsolvent evaporated

Sources & evidence

ORD record
ord-85dae12d167240cbbe3aa5e9a38e53ef
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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