N-Aminomorpholine → HCID 86659722, compound

HRID 1878561Notes

Reaction equation

HRID 1878561 reaction equation
BrC1C=CC([C:8]2[CH:23]=[C:11]3[N:12]=[C:13]([Cl:22])[CH:14]=[C:15]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:10]3[N:9]=2)=CC=1.[CH3:24][C:25](C)([O-])[CH3:26].[Na+].C(P([C:39]([CH3:42])([CH3:41])C)C(C)(C)C)(C)(C)C.[NH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O>[Cl:22][C:13]1[CH:14]=[C:15]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[N:10]2[N:9]=[C:8]([N:43]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[C:41]3[CH:39]=[CH:42][CH:26]=[CH:25][CH:24]=3)[CH:23]=[C:11]2[N:12]=1

Participants

8

Reactant 4

HCID 20315N-AminomorpholineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 58531012HCID 58531012, compound

Product 1

HCID 86659722HCID 86659722, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(4-bromophenyl)-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]-pyrimidine (100 mg, 0.25 mM) in toluene (7.0 mL), there were, in order, added sodium tert-butoxide (49 mg, 0.51 mM), tris(dibenzylidene-acetone) dipalladium (12 mg, 0.013 mM), tri-tert-butyl-phosphine (25 μL, 0.10 mM) and N-amino-morpholine (39 mg, 0.38 mM) and the mixture was stirred at 90° C. for 4 hours. After cooling the mixture to room temperature, water was added thereto and the mixture was extracted with ethyl acetate. The organic phase thus obtained was washed with a saturated aqueous common salt solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was washed with methanol to thus give the title compound (62 mg, yield: 60%).

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic phase thus obtained
  4. washwas washed with a saturated aqueous common salt solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting residue was washed with methanol

Sources & evidence

ORD record
ord-c2fa0bd5796f4790ac2a84c3b577952d
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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