HCID 58446972, compound → HCID 58446997, compound

HRID 1045774Notes

Reaction equation

HRID 1045774 reaction equation
[Br:1][C:2]1[C:3]([N:21]=[CH:22][NH:23]O)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1>[OH-].[K+]>[Br:1][C:2]1[C:3]2[N:4]([N:23]=[CH:22][N:21]=2)[C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 58446972HCID 58446972, compound

Product 1

HCID 58446997HCID 58446997, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A 100 mL round bottom flask was charged with tert-butyl 4-(5-bromo-4-(((hydroxyamino)methylene)amino)pyrimidin-2-yl)piperazine-1-carboxylate (1.1 g) and polyphosphoric acid (20 g). The resulting mixture was stirred at 100° C. overnight. Work-up: the reaction mixture was carefully diluted with saturated aqueous KOH (300 mL) and then extracted with CH2Cl2 (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford 0.3 g (39%) of the product as a white solid. MS m/z: 283 (M+H+).

Workup

  1. extractionextracted with CH2Cl2 (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-65e29874661e4830b05b7ac650b65b14
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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