Benzylamine → HCID 69798198, compound

HRID 586366Notes

Reaction equation

HRID 586366 reaction equation
[N:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]([C:10]([OH:12])=O)=[N:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl.C(OCC)(=O)C>[CH2:17]([N:24]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([C:4]1[CH:5]=[C:6]([C:7]([OH:9])=[O:8])[N:1]=[CH:2][N:3]=1)=[O:12])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 24386Thionyl ChlorideHCID 239360pyrimidine-4,6-dicarboxylic acid

Product 1

HCID 69798198HCID 69798198, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
24 °C

Procedure

Pyrimidine-4,6-dicarboxylic acid is dissolved in dichloromethane (DCM) at 24° C. To the solution is added three equivalents of thionyl chloride. The reaction mixture is stirred at 24° C. for 1 hour. The reaction mixture is concentrated by evaporation of the solvent under reduced pressure to give an oil. The oil is dissolved in ethyl acetate, and three equivalents of benzylamine are added. The reaction mixture is stirred at 24° C. for 3 hours. The solvent is than removed by evaporation under reduced pressure to give an oil. The oil is purified by chromatography over silica gel, eluting with hexane-ethyl acetate (9:1) to 100% ethyl acetate. The fractions shown by thin layer chromatography to contain a single product component are combined and concentrated to dryness under reduced pressure to give the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation of the solvent under reduced pressure
  2. customto give an oil
  3. stirringThe reaction mixture is stirred at 24° C. for 3 hours
  4. customthan removed by evaporation under reduced pressure
  5. customto give an oil
  6. customThe oil is purified by chromatography over silica gel
  7. washeluting with hexane-ethyl acetate (9:1) to 100% ethyl acetate
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-472a495895b2430ab7d7b6c3c2c71772
Source dataset
uspto-grants-2005_08
Patent number
US06936616B2

Reaction notes

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