Dichloromethane → HCID 59834669, compound

HRID 271598Notes

Reaction equation

HRID 271598 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:32]=[CH:31][C:13]([CH2:14][C:15]2[N:25]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]3[N:19]=[C:20]([C:23]#[N:24])[N:21]=[CH:22][C:17]=3[CH:16]=2)=[CH:12][CH:11]=1.C(Cl)Cl>CN(C=O)C.CO>[CH3:28][C:27]([CH3:30])([CH3:29])[CH2:26][N:25]1[C:18]2[N:19]=[C:20]([C:23]#[N:24])[N:21]=[CH:22][C:17]=2[CH:16]=[C:15]1[CH2:14][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 17968264HCID 17968264, compound

Product 1

HCID 59834669HCID 59834669, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

1,2,4-Triazole (0.6 mmol) is dissolved in DMF (1 ml) and sodium hydride (0.6 mmol) is added. The mixture is stirred and 6-(4-bromomethyl-benzyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.5 mmol) in DMF (1 ml) is added at 0° C. The mixture is stirred at room temperature for 0.5 h, and quenched with H2O. The mixture is extracted with AcOEt. The organic layer is washed with water and brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give the product in 57% yield. Rf=0.50 (CH2Cl2:MeOH=9:1). 1H NMR (400 MHz, CDCl3) δ 1.04(s, 9H), 4.06(s, 2H), 4.22(s, 2H), 5.36(s, 2H), 6.22(s, 1H), 7.18(d, 2H), 7.23-7.39(m, 2H), 7.98(s, 1H), 8.09(s, 1H), 8.83(s, 1H).

Workup

  1. stirringThe mixture is stirred at room temperature for 0.5 h
  2. customquenched with H2O
  3. extractionThe mixture is extracted with AcOEt
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography
  8. customto give the product in 57% yield

Sources & evidence

ORD record
ord-20b419c9825f45c28935be8dc2d92af8
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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