Diisopropylethylamine → HCID 86654886, compound

HRID 883836Notes

Reaction equation

HRID 883836 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[NH:16][N:15]=[C:14]([CH3:17])[CH:13]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:10][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[C:7]=1[CH:8]=[N:11][C:12]1[N:16]2[N:15]=[C:14]([CH3:17])[CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehydeHCID 178418690HCID 178418690, compound

Product 1

HCID 86654886HCID 86654886, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 1a (1.24 g, 7.01 mmol) in 30 mL of THF was reacted with 5-amino-3-methylpyrazole (0.68 g, 7.01 mmol) in 10 mL of THF under an argon atmosphere by dropwise addition. Stirred at room temperature for 1 hour than added diisopropylethylamine (1.22 mL, 7.01 mmol) dropwise with stirring. Heated overnight at 60° C. Quenched with water and extracted with EtOAc washed with brine and dried over Na2SO4. Filtered and the solvent was removed under vacuum. The product was purified by silica gel chromatography eluting with EtOAc/hexane to give the title compound as a pale yellow solid (405 mg, 29%).

Workup

  1. stirringwith stirring
  2. temperatureHeated overnight at 60° C
  3. customQuenched with water
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltered
  8. customthe solvent was removed under vacuum
  9. customThe product was purified by silica gel chromatography
  10. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-a183d5c576524c1eb0e87c44d589b425
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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