1,2-Diaminocyclohexane, trans- → HCID 57762549, compound

HRID 1365651Notes

Reaction equation

HRID 1365651 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[C@@H:15]1(N)[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1N.CC(C)([O-])C.[Na+]>O1CCOCC1.[Cu](I)I>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 438061,2-Diaminocyclohexane, trans-HCID 22346771HCID 22346771, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 57762549HCID 57762549, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Under an argon atmosphere, a suspension of N-(4-bromophenyl)pyrimidin-2-amine (250 mg), copper iodide (1.9 mg), trans-1,2-cyclohexanediamine (0.015 ml) and sodium-tert-butoxide (144 mg) in dioxane (1 ml) was stirred at 110° C. for 22 hours in a pressure-resistant test tube. The reaction solution was filtered and the filtrate was concentrated. The residue was purified by thin layer chromatography (silica gel, mobile phase: chloroform/ethyl acetate=5/1) to obtain N-(4-bromophenyl)-N-phenylpyrimidin-2-amine (56 mg).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by thin layer chromatography (silica gel, mobile phase: chloroform/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-5c165640ab7f499d81d0e8ccd819cac7
Source dataset
uspto-grants-2011_02
Patent number
US07893046B2

Reaction notes

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