Dichloromethane → 2-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol

HRID 515245Notes

Reaction equation

HRID 515245 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH3:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([Cl:18])[N:12]=1.C(Cl)Cl>C(N(CC)CC)C>[Cl:18][C:13]1[N:12]=[C:11]([CH3:10])[N:16]=[C:15]([N:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]2)[CH:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 76771-(2-Hydroxyethyl)piperazine2×HCID 2349974,6-Dichloro-2-methylpyrimidine2×

Product 1

HCID 144795582-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanolYield 89.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
30 °C

Procedure

1-(2-hydroxyethyl)piperazine (Compound 3) (16.6 g, 127.6 mmol)) and 2-methyl-4,6-dichloropyrimidine (Compound 2) (10.4 g, 63.8 mmol) were mixed with methylene dichloride (80 mL) in reaction flask to be stirred for 2.5 h at 30° C., and then triethylamine (1.8 mL) was added with the reaction overnight in thermal insulation. After vacuum filtration, the cake was rinsed by methylene dichloride. The filtrate was vacuum condensed to dry, and then n-hexane (40 mL) was added to grow the grains for 1 h by stirring. After vacuum filtration, the cake was rinsed by n-hexane (20 mL) and dried at 40° C. to constant weight to give white solid target Compound 4 (14.7 g, yield: 89.8%).

Workup

  1. filtrationAfter vacuum filtration
  2. washthe cake was rinsed by methylene dichloride
  3. customvacuum condensed
  4. customto dry
  5. additionn-hexane (40 mL) was added
  6. customfor 1 h
  7. stirringby stirring
  8. filtrationAfter vacuum filtration
  9. washthe cake was rinsed by n-hexane (20 mL)
  10. customdried at 40° C. to constant weight

Sources & evidence

ORD record
ord-9c2895924dc74897ab2ed8b4c70ac49f
Source dataset
uspto-grants-2015_08
Patent number
US09108954B2

Reaction notes

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