Benzoyl chloride → HCID 67251365, compound

HRID 2421007Notes

Reaction equation

HRID 2421007 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[C:7](SC)[N:6]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=O)C=1.ClCCl.C(=O)([O-])O.[Na+].[N:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][NH2:42])=[CH:36][CH:35]=1.C(Cl)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl.ClCCl>[C:11]([C:10]1[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[N:6][C:7]([NH:42][CH2:41][CH2:40][C:37]2[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=2)=[N:8][CH:9]=1)#[N:12]

Participants

8

Reactant 5

HCID 7412Benzoyl chlorideHCID 832754-PyridineethanamineHCID 516892Sodium BicarbonateHCID 67252215HCID 67252215, compoundHCID 86626010HCID 86626010, compound

Product 1

HCID 67251365HCID 67251365, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 40 mL of dichloromethane, 4-n-propylamino-5-cyano-2-methylthiopyrimidine obtained in Step 1 was dissolved, then mCPBA-dichloromethane solution (0.50 mol/L, 25 mL, 12.5 mmol) was added thereto over 5 minutes, followed by stirring at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then the solvent evaporated under reduced pressure. The residue was dissolved in THF (40 mL), then 2-(4-pyridyl)ethylamine (1.47 g, 12.0 mmol) was added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction was confirmed by thin-layer chromatography, chloroform (80 mL), benzoylchloride polymer bound [about 2.5 mmol/g, 4.6 g, Canadian Journal of Chemistry, Vol. 55, p. 3351 (1977)] and poly(4-vinylpyridine) (4.6 g) were added thereto, followed by further stirring at room temperature for 12 hours. After resins in the reaction mixture were filtered out, the filtrate was concentrated to give 5-cyano-4-n-propylamino-2-[2-(4-pyridyl)ethylamino]pyrimidine [Compound (Y) in which R1 is n-propylamino and R1 is 2-(4-pyridyl)ethylamino].

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in THF (40 mL)
  6. stirringby stirring at room temperature for 12 hours
  7. additionwere added
  8. stirringby further stirring at room temperature for 12 hours
  9. filtrationAfter resins in the reaction mixture were filtered out
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-669f837bfbe34762b8f941760d3508ad
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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