Methanol → HCID 86636943, compound

HRID 1366453Notes

Reaction equation

HRID 1366453 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 66936088(R)-1,2-Dimethyl-piperazine dihydrochloride

Product 1

HCID 86636943HCID 86636943, compoundYield 94%

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 (2R)-1,2-dimethylpiperazine dihydrochloride (0.189 g, 1.0 mmol) in THF (10 mL) was added triethylamine (0.42 mL, 3.0 mmol). MeOH (1 mL) was added to improve solubility. Reaction left to stir overnight. The solvent was removed in vacuo, and THF and ether were added to the resulting residue, which was washed with water. The organics were dried (Na2SO4) and concentrated in vacuo to provide 4-chloro-6-[(3R)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine as a yellow oil (0.242 g, 94%). LCMS: (M+H)+=259.3.

Workup

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

Sources & evidence

ORD record
ord-de493923feab45a58d959e94330135ad
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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