1-Methylpiperazine → 4-Chloro-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

HRID 2090280Notes

Reaction equation

HRID 2090280 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:8][C:6]1[CH:5]=[C:4]([N:14]2[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]2)[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 655222-Amino-4,6-dichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 14845194-Chloro-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-Amino-4,6-dichloropyrimidine (1.0 g, 6.1 mmol, Alfa Aesar, Cat. No. A11330), 1-methyl piperazine (0.74 mL, 6.7 mmol, Aldrich, Cat. No. 130001), and N,N-diisopropylethylamine (1.3 mL, 7.3 mmol) in isopropyl alcohol (5 mL) was heated at 110° C. for 2 hours. The reaction mixture was cooled to room temperature (r.t.). The precipitate formed was filtered and then washed by a small amount of isopropanol. The precipitate collected was dried under vacuum to afford this compound and used in the next step without further purification. LCMS(M+H)+: m/z=228.1.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed by a small amount of isopropanol
  4. customThe precipitate collected
  5. customwas dried under vacuum
  6. customto afford this compound
  7. customused in the next step without further purification

Sources & evidence

ORD record
ord-1b2b37d604ab43689907593f78241eb9
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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