1-(2-Methoxyphenyl)piperazine → 7-(2,2-Dimethyl-propyl)-6-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271557Notes

Reaction equation

HRID 271557 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.Br[CH2:18][C:19]1[N:29]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:22]2[N:23]=[C:24]([C:27]#[N:28])[N:25]=[CH:26][C:21]=2[CH:20]=1>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[CH3:32][C:31]([CH3:34])([CH3:33])[CH2:30][N:29]1[C:22]2[N:23]=[C:24]([C:27]#[N:28])[N:25]=[CH:26][C:21]=2[CH:20]=[C:19]1[CH2:18][N:14]1[CH2:15][CH2:16][N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH3:3])[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 24758Sodium hydrideHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Product 1

HCID 101803127-(2,2-Dimethyl-propyl)-6-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileYield 83.4%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (0.91 mmol) in DMF (10 ml), 1-(2-methoxyphenyl)piperazine (1.04 mmol) and 18-crown-6 (0.003 mmol) are successively added at 0° C. To the mixture, 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.65 mmol) is added at 0° C. and the mixture is stirred for 2 h at ambient temperature. The reaction mixture is quenched with ice-water and extracted with AcOEt. The combined extracts are washed with H2O, brine and dried over magnesium sulfate. Chromatography on silica gel (eluent; n-hexane:AcOEt=1:1) give 227 mg of desired 7-(2,2-Dimethyl-propyl)-6-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 83% yield.

Workup

  1. additionare successively added at 0° C
  2. customThe reaction mixture is quenched with ice-water
  3. extractionextracted with AcOEt
  4. washThe combined extracts are washed with H2O, brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-c973aba360934efbbb6ce83135bca352
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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