Methylamine → HCID 19709738, compound

HRID 725829Notes

Reaction equation

HRID 725829 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9](Cl)[N:8]2[N:12]=[CH:13][CH:14]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])O.[Na+].[CH3:20][NH2:21]>C(O)C>[CH2:1]([C:5]1[CH:10]=[C:9]([NH:21][CH3:20])[N:8]2[N:12]=[CH:13][CH:14]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 22618004HCID 22618004, compound

Product 1

HCID 19709738HCID 19709738, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
120 °C

Procedure

5-n-Butyl-7-chloropyrazolo[1,5-a]pyrimidine (the compound prepared in step (2) of Reference Example 1; 8.60 g), sodium hydrogen carbonate (3.44 g) and 40% methylamine (3.18 g) were added to 50 ml of ethanol and heated at 120° C. for 2 hours. After completion of the reaction, ethanol was distilled off under reduced pressure. After addition of some water, the residue was extracted with ethyl acetate. The organic layer was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:2) to provide 2.33 g of 5-n-butyl-7-methylaminopyrazolo[1,5-a]pyrimidine as crystals.

Workup

  1. distillationwas distilled off under reduced pressure
  2. additionAfter addition of some water
  3. extractionthe residue was extracted with ethyl acetate
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-69dbd2cfad37424f863c2b24c0851ebc
Source dataset
uspto-grants-1998_01
Patent number
US05707997

Reaction notes

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