Methanol → HCID 59834720, compound

HRID 271597Notes

Reaction equation

HRID 271597 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].Br[CH2:10][C:11]1[CH:33]=[CH:32][C:14]([CH2:15][C:16]2[N:26]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:19]3[N:20]=[C:21]([C:24]#[N:25])[N:22]=[CH:23][C:18]=3[CH:17]=2)=[CH:13][CH:12]=1.C(Cl)Cl.CO>CN(C=O)C.CCOC(C)=O>[CH3:29][C:28]([CH3:30])([CH3:31])[CH2:27][N:26]1[C:19]2[N:20]=[C:21]([C:24]#[N:25])[N:22]=[CH:23][C:18]=2[CH:17]=[C:16]1[CH2:15][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 791961-EthylpiperazineHCID 17968264HCID 17968264, compound

Product 1

HCID 59834720HCID 59834720, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Ethyl-piperazine (1.1 mmol) and 6-(4-bromomethyl-benzyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.35 mmol) are dissolved in DMF (3 ml) and stirred at room temperature for 3 h. After the reaction mixture is diluted with AcOEt, the organic layer is washed with brine, dried over magnesium sulfate and filtrated. The solvent is evaporated and the residue is purified by chromatography on silica gel using 2% MeOH in CH2Cl2 and 7% MeOH in CH2Cl2. The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford crystals. yield 81.8%, Rf=0.34 (CH2Cl2:MeOH=9:1).

Workup

  1. washthe organic layer is washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. customThe solvent is evaporated
  5. customthe residue is purified by chromatography on silica gel using 2% MeOH in CH2Cl2 and 7% MeOH in CH2Cl2
  6. customThe solvent of the latter effluent is removed by evaporation
  7. customdried in vacuo
  8. customto afford crystals

Sources & evidence

ORD record
ord-1aa6c2972a07429db2228bad95791953
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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