Morpholine → HCID 57972813, compound

HRID 661468Notes

Reaction equation

HRID 661468 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[CH2:28]([O:35][C:36]1[N:41]=[CH:40][C:39](Br)=[CH:38][N:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O>[CH2:28]([O:35][C:36]1[N:41]=[CH:40][C:39]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)=[CH:38][N:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

9

Reactant 4

HCID 8083MorpholineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 425530552-(Benzyloxy)-5-bromopyrimidine

Product 1

HCID 57972813HCID 57972813, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Tris(dibenzylideneacetone)dipalladium (1.78 g), 2-(di-tert-butylphosphino)-biphenyl (2.32 g) and sodium tert-butoxide (4.49 g) were added to a solution of 2-benzyloxy-5-bromo-pyrimidine (10.3 g) and morpholine (4.1 ml) in toluene (180 ml) and the mixture was stirred under nitrogen atmosphere at 50° C. for an hour. The reaction mixture was cooled to room temperature. Water and ethyl acetate were added and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with ethyl acetate and hexane to give the titled compound (9.12 g). MS (m/z): 272 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. washwashed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-e0b3f5b25dd94e04965451245aef9f4f
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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