Methanol → HCID 86636941, compound

HRID 1366447Notes

Reaction equation

HRID 1366447 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.Cl.Cl.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C@@H:15]1[CH3:20].C(N(CC)CC)C.CO>C1COCC1>[Cl:9][C:6]1[C:7]([F:8])=[C:2]([N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[C@@H:15]([CH3:20])[CH2:16]2)[N:3]=[C:4]([CH3:10])[N:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidineHCID 66935895(2S)-1,2-Dimethylpiperazine--hydrogen chloride (1/2)

Product 1

HCID 86636941HCID 86636941, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-dichloro-5-fluoro-2-methylpyrimidine (0.181 g, 1.0 mmol) and (2S)-1,2-dimethylpiperazine dihydrochloride (0.189 g, 1.0 mmol) in THF (10 mL) was added triethylamine (0.42 mL, 3.0 mmol) at room temperature. MeOH (1 mL) was added to improve solubility. The reaction mixture was stirred overnight, and then the solvent was removed in vacuo. Ether, THF and water were added to the resulting residue. The organics were separated, dried (Na2SO4) and evaporated to provide 4-chloro-6-[(3S)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine as a yellow solid (0.254 g, 98%). LCMS: (M+H)+=259.3.

Workup

  1. customthe solvent was removed in vacuo
  2. additionEther, THF and water were added to the resulting residue
  3. customThe organics were separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-bec9a4f737794259aaa9ed18cef41c75
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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