Hexane → HCID 17968222, compound

HRID 271563Notes

Reaction equation

HRID 271563 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCC>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 59834726HCID 59834726, compound

Product 1

HCID 17968222HCID 17968222, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

7-(2,2-Dimethyl-propyl)-6-piperazin-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.4 mmol) and 1-bromomethyl-4-fluoro-benzene (0.6 mmol) is dissolved in DMF (5 ml) and potassium carbonate (0.6 mmol) is added to the solution. The reaction mixture is heated at 50° C. for 3 h. After the mixture is diluted with AcOEt, the organic layer is washed with brine, dried over magnesium sulfate and filtrated. AcOEt is evaporated and the residue is purified by reverse phase HPLC. The product is obtained in 90.5% yield. Rf=0.32 (n-hexane:AcOEt=1:5).

Workup

  1. washthe organic layer is washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. customAcOEt is evaporated
  5. customthe residue is purified by reverse phase HPLC
  6. customThe product is obtained in 90.5% yield

Sources & evidence

ORD record
ord-3ff7d5f596f4442ba612e58b552f21c4
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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