1-Methylpiperazine → 1231220-79-3

HRID 888980Notes

Reaction equation

HRID 888980 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[C:8](Cl)=[N:9][C:10]([CH3:20])=[N:11][C:12]=1[NH:13][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=O.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]1[N:13]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:12]2[C:7]([N:6]=1)=[C:8]([N:30]1[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]1)[N:9]=[C:10]([CH3:20])[N:11]=2

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 86642733HCID 86642733, compound

Product 1

HCID 468337801231220-79-3Yield 88.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
160 °C

Procedure

Combine 2-chloro-N-(4-chloro-2-methyl-6-(tetrahydro-2H-pyran-4-ylamino)-pyrimidin-5-yl) benzamide (45.0 g, 118.0 mmol), 1-methylpiperazine (23.0 mL, 207.0 mmol), di-isopropylethylamine (23.0 mL, 131.9 mmol) and isopropyl alcohol (225 mL) in a 1 L Parr reactor. Seal the reactor, start stirring, and adjust the set-point for heat control to 160° C. After the internal temperature reaches 160° C., stir the mixture for 24 hours. Cool the reactor contents to 60° C., vent the vessel of pressure, and transfer the contents to a 2 L flask equipped with overhead stirring apparatus. Rinse out reactor flask with isopropyl alcohol (25.0 mL) and combine the rinse with main solution. Add cold, de-ionized water (780 mL) to the mixture over 30 minutes and stir the resulting precipitate for 30 minutes. Filter the mixture, wash the solids with de-ionized water (2×270 mL) and pull dry on the funnel Further dry the product overnight at 45° C. to afford the 8-(2-Chloro-phenyl)-2-methyl-6-(4-methyl-piperazin-1-yl)-9-(tetrahydro pyran-4-yl)-9H-purine as an off-white solid (44.8 g) MS (m/z): 427/429 (M+1).

Workup

  1. customSeal the reactor
  2. customreaches 160° C.
  3. stirringstir the mixture for 24 hours
  4. temperatureCool the reactor contents to 60° C.
  5. customequipped with overhead stirring apparatus
  6. washRinse out reactor flask with isopropyl alcohol (25.0 mL)
  7. washrinse with main solution
  8. additionAdd cold
  9. stirringstir the resulting precipitate for 30 minutes
  10. filtrationFilter the mixture
  11. washwash the solids with de-ionized water (2×270 mL)
  12. custompull dry on the funnel
  13. customFurther dry the product overnight at 45° C.

Sources & evidence

ORD record
ord-d8a20e21a13741769c73a69c8fba1b1b
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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