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

HRID 1014929Notes

Reaction equation

HRID 1014929 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.CCN(CC)CC>CCO>[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 8471TriethylamineHCID 531671-MethylpiperazineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 14845194-Chloro-6-(4-methylpiperazin-1-yl)pyrimidin-2-amineYield 71.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino-4,6-dichloropyrimidine (15 g, 91 mmol) was treated with 1-methylpiperazine (10.1 g, 100 mmol), treated with Et3N (90 mL, 0.64 mol), treated with EtOH (185 mL), heated to 80° C. over night, cooled, concentrated and partitioned between CH2Cl2 (100 mL) and 1 M NaOH (125 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (4×100 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated and crystallized from EtOAc to provide 14.9 g (71%) of the title compound. 1H NMR (CDCl3) δ 2.34 (s, 3H), 2.45 (m, 4H), 3.60 (m, 4H), 4.82 (s, 2H), 5.96 (s, 1H); MS (DCl—NH3) m/z 228 (M+H)+

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. custompartitioned between CH2Cl2 (100 mL) and 1 M NaOH (125 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (4×100 mL)
  6. dry with materialThe combined CH2Cl2 layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customcrystallized from EtOAc

Sources & evidence

ORD record
ord-b7d2d40b4acc4813a889a3b0b69d73c2
Source dataset
uspto-grants-2011_07
Patent number
US07985745B2

Reaction notes

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