Sodium Hydroxide → HCID 178482353, compound

HRID 1743801Notes

Reaction equation

HRID 1743801 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:16])[C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[Br:17][CH2:18]/[CH:19]=[CH:20]/[CH2:21]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:17][CH2:18]/[CH:19]=[CH:20]/[CH2:21][O:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([N:8]([C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH3:16])[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 641245trans-1,4-Dibromo-2-butene2×HCID 178482352HCID 178482352, compound

Product 1

HCID 178482353HCID 178482353, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.47 g (8.62 mmol) of trans-4-[(5-Bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexanol, 5.53 g (25.86 mmol) of trans-1,4-dibromo-2-butene and 0.87 g (2.57 mmol, 0.3 eq) tetrabutylammoniumhydrogensulfate in 55 ml CH2Cl2 were treated with 55 ml of 50% aqueous NaOH. The mixture was stirred at RT for 40 h, 2.76 g (12.93 mmol) of trans-1,4-dibromo-2-butene were added and stirred for further 60 h. Then CH2Cl2 was added and the layers were separated. The inorganic layer was extracted with CH2Cl2 (3×), the combined organic layers washed with brine and dried over Na2SO4. The residue was purified by column chromatography on silica gel with hexane:EtOAc (9:1 to 2:1) as eluent yielding 0.8 g (22%) trans-(2E)-[4-(4-Bromo-but-2-enyloxy)-cyclohexyl]-(5-bromo-pyrimidin-2-yl)-methyl-amine as light yellow solid, MS: 418 (MH+, 2Br).

Workup

  1. stirringstirred for further 60 h
  2. customthe layers were separated
  3. extractionThe inorganic layer was extracted with CH2Cl2 (3×)
  4. washthe combined organic layers washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe residue was purified by column chromatography on silica gel with hexane:EtOAc (9:1 to 2:1) as eluent

Sources & evidence

ORD record
ord-f0ced33f55a946dbad9e04ac9ba32402
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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