Benzyl Bromide → HCID 178526824, compound

HRID 1819414Notes

Reaction equation

HRID 1819414 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH2:32]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:30])([F:31])[F:29])[N:11]=2)[CH2:6][CH2:7]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 178511544HCID 178511544, compound

Product 1

HCID 178526824HCID 178526824, compoundYield 6.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]-pyrimidine-2,4-diamine (100 mg, 0.23 mmol) in DMF (3 mL) were added benzyl bromide (39 mg, 0.23 mmol) followed by DIPEA (40 μL, 0.23 mmol). The reaction mixture was stirred at room temperature for 20 h. The reaction mixture was diluted with EtOAc and washed with water (×4). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel prep TLC using 10:1 CH2Cl2:MeOH as an eluent to afford 8 mg of the title compound, m/z 531.6 [M+1]+.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-f6b00996e9194568a177dd0b06b13545
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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