Triethylamine → HCID 59834681, compound

HRID 271577Notes

Reaction equation

HRID 271577 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[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][C:19](=O)[CH2:18][CH2:17]1.[N:25]1N=CN(N)C=1.C(N(CC)CC)C.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO.CC(C)=O>[NH2:25][CH:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:5]2[N:4]([CH2:3][C:2]([CH3:24])([CH3:23])[CH3:1])[C:8]3[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=3[CH:6]=2)[CH2:17][CH2:18]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 114324-Amino-1,2,4-triazoleHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 9880368HCID 9880368, compound

Product 1

HCID 59834681HCID 59834681, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the mixture of 100 mg (0.30 mmoles) of 7-(2,2-Dimethyl-propyl)-6-(4-oxo-piperidin-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile, 40 mg (0.60 mmoles) of [1,2,4]triazol-4-ylamine and 0.16 ml (1.1 mmoles) of triethylamine in 5 ml of CH2Cl2, 58 mg (0.48 mmoles) of MgSO4 is added at ambient temperature and the mixture is stirred for 17.5 hours at ambient temperature. The reaction mixture is filtered to remove MgSO4 and concentrated under reduced pressure to give crude imine. To a solution of crude imine in 5 ml of MeOH, 13 mg (0.33 mmoles) of NaBH4 is added at −10-−20° C., and the reaction mixture is stirred at 0° C. for 1 h. After addition of 5 ml of acetone, the mixture is concentrated, diluted with H2O, and then extracted with CH2Cl2. The combined extrats are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 85 mg of desired 6-(4-amino-piperidin-1-ylmethyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 85% yield.

Workup

  1. additionis added at ambient temperature
  2. filtrationThe reaction mixture is filtered
  3. customto remove MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give crude imine
  6. stirringthe reaction mixture is stirred at 0° C. for 1 h
  7. concentrationthe mixture is concentrated
  8. additiondiluted with H2O
  9. extractionextracted with CH2Cl2
  10. washThe combined extrats are washed with brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under reduced pressure
  13. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa6e4d476b8147568ea30f3f2ad6d29a
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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