Morpholine → 4-(5-Methylsulfanyl-4,6-di-morpholin-4-yl-pyrimidin-2-yl)-phenylamine

HRID 629036Notes

Reaction equation

HRID 629036 reaction equation
Cl[C:2]1[C:7]([S:8][CH3:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[N:3]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(N(CC)CC)C>O1CCOCC1>[CH3:9][S:8][C:7]1[C:2]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:3][C:4]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)=[N:5][C:6]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86673495HCID 86673495, compound

Product 1

HCID 866735174-(5-Methylsulfanyl-4,6-di-morpholin-4-yl-pyrimidin-2-yl)-phenylamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (200 mg, 0.594 mmol.), morpholin (103 mg, 1.118 mmol, 2.0 eq), triethylamine (120 mg, 1.118 mmol, 2.0 eq) in dioxane (8 ml) and the mixture was reacted for 16 hrs at 90° C. The reaction mixture was dried and the solvent was removed by evaporation in vacuo. The reaction mixture was partitioned between EA and water. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified using flash chromatography on silica gel (EA), and recrystallized by (Hexane/EtOAc) to give a gray white 106 mg (46.1%).

Workup

  1. customthe mixture was reacted for 16 hrs at 90° C
  2. customThe reaction mixture was dried
  3. customthe solvent was removed by evaporation in vacuo
  4. customThe reaction mixture was partitioned between EA and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe resulting residue was purified
  10. customrecrystallized by (Hexane/EtOAc)
  11. customto give a gray white 106 mg (46.1%)

Sources & evidence

ORD record
ord-4aa9264242334519911cb0f0d020de90
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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