Triethylamine → HCID 178445669, compound

HRID 1458661Notes

Reaction equation

HRID 1458661 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[C:9]([C@@H:13]1[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15][CH2:14]1)([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:9]([C@@H:13]1[CH2:14][CH2:15][C@H:16]([NH:19][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)[CH2:17][CH2:18]1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 178445676HCID 178445676, compound

Product 1

HCID 178445669HCID 178445669, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

58.6 g (0.39 mol) of 4,6-dichloropyrimidine were placed in 400 ml of toluene, and a mixture of 61.0 g (0.39 mol) of cis-4-tert-butylcyclohexylamine and 50.0 g (0.50 mol) of triethylamine in 100 ml of toluene was added dropwise at from 70° to 80° C. The mixture was subsequently stirred at reflux for 4 hours. After cooling, it was extracted by stirring with water, the organic phase was dried and concentrated, to give a colorless oil which crystallized after trituration with petroleum ether. Filtration with suction left 70.5 g (67.0% of theory) of colorless crystals.

Workup

  1. additionwas added dropwise at from 70° to 80° C
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling
  4. extractionit was extracted
  5. stirringby stirring with water
  6. customthe organic phase was dried
  7. concentrationconcentrated
  8. customto give a colorless oil which
  9. customcrystallized after trituration with petroleum ether
  10. filtrationFiltration with suction
  11. waitleft 70.5 g (67.0% of theory) of colorless crystals

Sources & evidence

ORD record
ord-86925259218146fc833252ccebbb8e15
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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