Morpholine → HCID 15547786, compound

HRID 2268011Notes

Reaction equation

HRID 2268011 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:19]([CH3:22])([CH3:21])[OH:20])[CH:5]=[C:6]([O:17][CH3:18])[C:7]=1[O:8][C:9]1[N:14]=[C:13](Cl)[N:12]=[C:11]([CH3:16])[N:10]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:19]([CH3:22])([CH3:21])[OH:20])[CH:5]=[C:6]([O:17][CH3:18])[C:7]=1[O:8][C:9]1[N:14]=[C:13]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:12]=[C:11]([CH3:16])[N:10]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 15547795HCID 15547795, compound

Product 1

HCID 15547786HCID 15547786, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-4-[[4-chloro-6-methyl-1,3,5-triazin-2-yl]oxy]-5-methoxy-a,a-dimethylbenzenemethanol (3.0 g) in anhydrous 1,4-dioxane (80 mL), morpholine (1.39 mL) was added and the solution was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was taken up in water and extracted with methylene chloride. The extracts were combined and dried over MgSO4. The solvent was stripped under reduced pressure and the residue was purified on silica gel using a 2:1 mixture of ethyl acetate and hexane to yield 3-bromo-4-[[6-methyl-4-(4-morpholinyl)-1,3,5-triazin-2-yl]oxy]-5-methoxy-a,a-dimethylbenzenemethanol as a colorless powder, mp 199-201° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with methylene chloride
  3. dry with materialdried over MgSO4
  4. customthe residue was purified on silica gel using
  5. additiona 2:1 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-886941c1bfa84eb18bbf744a436a77db
Source dataset
uspto-grants-2001_12
Patent number
US06326368B1

Reaction notes

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