Triethylamine → HCID 18432574, compound

HRID 2305995Notes

Reaction equation

HRID 2305995 reaction equation
[CH2:1]([C:8]1[C:9](Cl)=[N:10][C:11]([Cl:14])=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](N(CC)CC)C.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(O)C>[Cl:14][C:11]1[N:10]=[C:9]([N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:16])=[CH:4][CH:3]=2)=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 18432575HCID 18432575, compound

Product 1

HCID 18432574HCID 18432574, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 5-benzyl-2,4-dichloropyrimidine (9.66 g, 38 mmoles), triethylamine (Aldrich) (4.15 g, 41 mmoles), and ethanol (20 mL) was stirred at ice bath temperature for 10 minutes. 1-Methylpiperazine (Aldrich) (3.83 g, 38 mmoles) in ethanol (10 mL) was added, and the reaction was stirred at ambient temperature for 16 hours. The solution was spin evaporated in vacuo at 40° C. to give a residue that was partitioned between dichloromethane (50 mL) and water (70 mL). The dichloromethane phase was separated and washed with water (2×7 mL), and finally with brine (50 mL). The dichloromethane solution was dried over sodium sulfate, filtered and applied to a column (4×20 cm) of Silica Gel 60 (230-400 mesh) that was equilibrated with dichloromethane. The column was eluted with dichloromethane (400 mL) by flash chromatography to remove impurities. The product was eluted with 2% methanol-dichloromethane, and the combined fractions were spin evaporated in vacuo to give 9.89 g (cc % yield) of 2-chloro-5-(4-methylbenzyl)-4-(4-methylpiperazino)pyrimidine.

Workup

  1. customevaporated in vacuo at 40° C.
  2. customto give a residue that
  3. customwas partitioned between dichloromethane (50 mL) and water (70 mL)
  4. customThe dichloromethane phase was separated
  5. washwashed with water (2×7 mL)
  6. dry with materialThe dichloromethane solution was dried over sodium sulfate
  7. filtrationfiltered
  8. washThe column was eluted with dichloromethane (400 mL) by flash chromatography
  9. customto remove impurities
  10. washThe product was eluted with 2% methanol-dichloromethane
  11. customthe combined fractions were spin evaporated in vacuo

Sources & evidence

ORD record
ord-51c760904b1a42fa9667a41e57578117
Source dataset
uspto-grants-2002_08
Patent number
US06440965B1

Reaction notes

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