HCID 18432581, compound → HCID 18432493, compound

HRID 2305992Notes

Reaction equation

HRID 2305992 reaction equation
[CH2:1]([C:8]1[C:9]([NH:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21])=[N:10][C:11](Cl)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[CH2:1]([C:8]1[C:9]([NH:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21])=[N:10][CH:11]=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 18432581HCID 18432581, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18432493HCID 18432493, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-benzyl-2-chloro-4-[2-(2-hydroxyethoxy)ethylamino]pyrimidine (3.50 g, 12.08 mmoles), ethanol (190 mL) and 10% Pd on carbon (Aldrich) (0.84 g) was shaken in to presence of hydrogen at 2-3 atm for 17 hours. The reaction mixture was filtered through a pad of CELITE®, and the filtrates were spin evaporated in vacuo. The residual syrup was dissolved in dichloromethane (40 mL) and washed with water (20 mL) brine (20 mL) and then dried over sodium sulfate. The dry solution was spin evaporated in vacuo to give a residue that was triturated under hexanes to give 0.15 g (5% yield) of 5-benzyl-4-[2-(2-hydroxyethoxy)ethylamino]pyrimidine as a white solid, mp 86-87° C.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE®
  2. customthe filtrates were spin evaporated in vacuo
  3. dissolutionThe residual syrup was dissolved in dichloromethane (40 mL)
  4. washwashed with water (20 mL) brine (20 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customto give a residue that
  8. customwas triturated under hexanes

Sources & evidence

ORD record
ord-afc3b2e9a3a9455fb5adb20750ec3ab3
Source dataset
uspto-grants-2002_08
Patent number
US06440965B1

Reaction notes

Loading…