Tetrahydrofuran → HCID 57962244, compound

HRID 541906Notes

Reaction equation

HRID 541906 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([Cl:26])[N:20]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH:5]=[N:6][CH:7]=1.O1CCCC1.C([O-])(=O)C.[Na+]>COCCOC.O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([Cl:26])[N:20]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 517045Sodium AcetateHCID 86636288HCID 86636288, compound

Product 1

HCID 57962244HCID 57962244, compoundYield 77.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-{3-[(E)-2-(5-aminopyridin-3-yl)vinyl]-4-methoxyphenyl}-2,5-dichloropyrimidin-4-amine (2.25 g, 5.80 mmol) in 1,2-dimethoxyethane (2.0 mL), and tetrahydrofuran (100 mL) was added p-toluenesulfonylhydrazide (16.2 g, 86.9 mmol). The reaction mixture was heated to 90° C. when a solution of sodium acetate (11.4 g, 139 mmol) in water (120 mL) was added dropwise over 4 h. The reaction mixture was stirred at 90° C. for 3 h. The reaction mixture was diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate twice. The combined organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give the desired product as a yellow foam (1.75 g, 77%). LCMS for C18H18Cl2N5O (M+H)+: m/z=390.1

Workup

  1. additionwas added dropwise over 4 h
  2. extractionThe aqueous layer was extracted with ethyl acetate twice
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-172ba62e2eca4313b9f83c37afd58c2f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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