Methanol → HCID 86636950, compound

HRID 1366471Notes

Reaction equation

HRID 1366471 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.C(N(CC)CC)C.Cl.Cl.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][C@@H:23]([CH3:27])[CH2:22]1.CO>C1COCC1>[Cl:9][C:6]1[C:7]([F:8])=[C:2]([N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][C@@H:23]2[CH3:27])[N:3]=[C:4]([CH3:10])[N:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidineHCID 66936682Piperazine, 1,3-dimethyl-, hydrochloride (1:2), (3S)-

Product 1

HCID 86636950HCID 86636950, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4,6-dichloro-5-fluoro-2-methylpyrimidine (0.309 g, 1.71 mmol) and triethylamine (0.83 mL, 5.98 mmol) in THF (6.0 mL) was added (3S)-1,3-dimethylpiperazine dihydrochloride (Example 64) (0.320 g, 1.71 mmol). MeOH (3 mL) was added to improve solubility and the reaction was stirred for 4 days at room temperature. The solvent was removed in vacuo, and ether, THF and water were added to the resulting residue. The organics were dried (Na2SO4) and concentrated in vacuo to provide 4-chloro-6-[(2S)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine as an orange solid (0.277 g, 63%). LCMS: (M+H)+=259.3.

Workup

  1. customThe solvent was removed in vacuo, and ether, THF and water
  2. additionwere added to the resulting residue
  3. dry with materialThe organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f2530eadebd4706839bdfb917c9f951
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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