Dichloromethane → 4-Methyl-2-(piperazin-1-yl)pyrimidine dihydrochloride

HRID 1775324Notes

Reaction equation

HRID 1775324 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[N:3]=1.C(Cl)[Cl:22]>FC(F)(F)C(O)=O>[ClH:22].[ClH:22].[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[N:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 15132529tert-Butyl 4-(4-methylpyrimidin-2-yl)piperazine-1-carboxylate

Product 1

HCID 183649784-Methyl-2-(piperazin-1-yl)pyrimidine dihydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The product from the previous step (tert-butyl 4-(4-methylpyrimidin-2-yl)piperazine-1-carboxylate) was dissolved in a one-to-one mixture of trifluoroacetic acid and DCM (8 ml) and stirred at room temperature for three hours. The volatiles were removed under reduced pressure, the residue was dissolved in DCM and evaporated. The residue was dissolved in THF (10 ml), HCl in dioxane (4N, 2 ml) was added and the resulting precipitate was collected by repeated centrifugation, dekantation and washing with THF to yield 107 mg of a solid (0.30 mmol, 71%). MS (APCI) m/z=179.1 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM
  3. customevaporated
  4. dissolutionThe residue was dissolved in THF (10 ml)
  5. additionHCl in dioxane (4N, 2 ml) was added
  6. customthe resulting precipitate was collected
  7. washwashing with THF

Sources & evidence

ORD record
ord-157bd86215b644048653cf862e9d567b
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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