Water → HCID 86725454, compound

HRID 2207116Notes

Reaction equation

HRID 2207116 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]([C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([CH2:18][CH2:19][O:20][CH3:21])[N:12]=1)([CH3:10])([CH3:9])[CH3:8].O>C(O)C>[C:7]([C:11]1[N:12]=[C:13]([CH2:18][CH2:19][O:20][CH3:21])[CH:14]=[C:15]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[N:16]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 86725452HCID 86725452, compound

Product 1

HCID 86725454HCID 86725454, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of piperazine (45.2 g, 525 mmol) in ethanol (300 mL) was heated to reflux. A solution of 2-tert-butyl-4-chloro-6-(2-methoxy-ethyl)-pyrimidine (20 g, 87 mmol) in ethanol (50 mL) was added dropwise to the above solution. The solution was refluxed for another 3 hrs, cooled to room temperature. Then water was added and the organic layer was extracted with EA (400 mL×3). To the organic layer was added 5% citric acid (1 L), separated, and the aqueous layer was collected and adjusted to alkaline pH>8 with 2 N NaOH. The alkaline aqueous layer was extracted with EA (400 mL×3), and the organic phase was dried over Na2SO4, filtered and concentrated to give the title compound (20 g, 82% yield) as a yellow oil.

Workup

  1. temperatureThe solution was refluxed for another 3 hrs
  2. extractionthe organic layer was extracted with EA (400 mL×3)
  3. additionTo the organic layer was added 5% citric acid (1 L)
  4. customseparated
  5. customthe aqueous layer was collected
  6. extractionThe alkaline aqueous layer was extracted with EA (400 mL×3)
  7. dry with materialthe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5f065abd1c9a47408506deb5f8e6574b
Source dataset
uspto-grants-2016_06
Patent number
US09376396B2

Reaction notes

Loading…