Potassium Carbonate → HCID 10095705, compound

HRID 2118052Notes

Reaction equation

HRID 2118052 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.Cl[C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][N:12]([C:29]4[N:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-Chloropyrimidine2×HCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 1

HCID 10095705HCID 10095705, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the amine from example 4 (200 mg, 0.53 mmol), 2-chloropyrimidine (66 mg, 0.58 mmol) and potassium carbonate (72 mg, 0.53 mmol) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 18 hours. TLC analysis showed starting materials remained, so additional 2-chloropyrimidine (66 mg, 0.58 mmol) was added, and the reaction was stirred at 80° C. for a further 72 hours. The cooled mixture was evaporated under reduced pressure, the residue was partitioned between ethyl acetate and brine, and the layers were separated. The organic layer was washed with water, wash with ammonium chloride solution, dried over magnesium sulphate and then evaporated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel using dichloromethane:methanol (95:5) as eluant, to afford the title compound as a yellow oil (117 mg).

Workup

  1. stirringthe reaction was stirred at 80° C. for a further 72 hours
  2. customThe cooled mixture was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and brine
  4. customthe layers were separated
  5. washThe organic layer was washed with water
  6. washwash with ammonium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customThe residual yellow oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7fabda50217441fe8a5e061ec598ca55
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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