Morpholine → HCID 53944659, compound

HRID 1907706Notes

Reaction equation

HRID 1907706 reaction equation
CS([C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]=1)(=O)=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>COCCOC.C(Cl)Cl>[O:19]1[CH2:20][CH2:21][N:16]([C:5]2[N:10]=[CH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

Product 1

HCID 53944659HCID 53944659, compoundYield 108%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of sulfone 121 (0.184 g, 0.80 mmol) in ethyleneglycol dimethylether (5 mL) was treated with neat morpholine (0.3 mL, 3.4 mmol) and the mixture was stirred at room temperature for 48 h. The reaction mixture was then diluted with DCM and washed with saturated NaHCO3 in brine, dried over MgSO4, filtered, concentrated and stored under vacuum to give intermediate 122 (0.205 g, >99% yield).

Workup

  1. washwashed with saturated NaHCO3 in brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dcd232c1eff14adbb87198f411184f79
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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