Morpholine → HCID 58531075, compound

HRID 1878539Notes

Reaction equation

HRID 1878539 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([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)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C1(C)C=CC=CC=1.O.[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>[Cl:22][C:13]1[CH:14]=[C:15]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:10]2[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:3][CH:4]=3)[CH:23]=[C:11]2[N:12]=1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 58531012HCID 58531012, compound

Product 1

HCID 58531075HCID 58531075, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

There was dissolved, in toluene (2 mL), 2-(4-bromo-phenyl)-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (41.7 mg, 0.106 mM) in an argon gas atmosphere and then there were added, to the resulting solution, sodium t-butoxide (15.3 mg, 0.159 mM), tris(dibenzylidene acetone) di-palladium (4.9 mg, 0.0053 mM), 2-biphenyl-di-t-butyl phosphine (4.7 mg, 0.016 mM) and morpholine (13.9 μL, 0.159 mM), followed by the stirring of the resulting mixture at 70° C. for 3 hours and the further stirring of the same at 90° C. for one hour. This reaction liquid was diluted with water and then extracted with ethyl acetate. The extracts thus obtained were combined, they were dried over anhydrous sodium sulfate, the solvent was distilled off and the resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:4) to thus give the title compound (15.6 mg, yield: 39%).

Workup

  1. stirringthe further stirring of the same at 90° C. for one hour
  2. customThis reaction liquid
  3. extractionextracted with ethyl acetate
  4. customThe extracts thus obtained
  5. dry with materialthey were dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:4)

Sources & evidence

ORD record
ord-26e912d5dfea46468a37487870ab3803
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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