2-Methoxyethylamine → HCID 86659715, compound

HRID 1878544Notes

Reaction equation

HRID 1878544 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+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH3:43][O:44][CH2:45][CH2:46][NH2:47]>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>[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]([NH:47][CH2:46][CH2:45][O:44][CH3:43])=[CH:3][CH:4]=3)[CH:23]=[C:11]2[N:12]=1

Participants

7

Reactant 4

HCID 80182-MethoxyethylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 58531012HCID 58531012, compound

Product 1

HCID 86659715HCID 86659715, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

There was dissolved, in toluene (3 mL), 2-(4-bromo-phenyl)-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (59.3 mg, 0.151 mM) in an argon gas atmosphere, then there were added, to the resulting solution, a solution of sodium t-butoxide (58.0 mg, 0.604 mM), tris(dibenzylidene acetone) di-palladium (6.9 mg, 0.0076 mM) and tri-t-butyl phosphine (11.0 μL, 0.0453 mM) in toluene (0.556 mL) and 2-methoxy-ethylamine (26.3 μL, 0.302 mM) and the resulting mixture was stirred at 80° C. for 4 hours and a half. This reaction liquid was diluted with a saturated aqueous common salt solution and then extracted with ethyl acetate. The extracts thus obtained were combined, dried over anhydrous sodium sulfate, then the solvent was distilled off and the resulting residue was purified by the silica gel column chromatography (ethyl acetate//hexane=1:4 to 2:3) to thus give the title compound (34.2 mg, yield: 58%).

Workup

  1. customThis reaction liquid
  2. additionwas diluted with a saturated aqueous common salt solution
  3. extractionextracted with ethyl acetate
  4. customThe extracts thus obtained
  5. dry with materialdried 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 to 2:3)

Sources & evidence

ORD record
ord-38a4892c2a494536bfb3c178630598a9
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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