Methyl iodide → HCID 68295953, compound

HRID 589975Notes

Reaction equation

HRID 589975 reaction equation
C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:36])(=[O:35])[NH:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.[C:37]([O-])([O-])=O.[K+].[K+].IC.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O.CCCCCCC.O>[CH3:37][N:26]([CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[S:25]([N:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:24][C:21]21[CH2:22][CH2:23]2)(=[O:35])=[O:36]

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 68295913HCID 68295913, compound2×

Product 1

HCID 68295953HCID 68295953, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

4-(4-Phenethylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 6) (0.78 mmol) was dissolved in dry DMF (5 mL) and added K2CO3 (1.56 mmol) and iodomethane (1.17 mmol). Stirred at rt for 3 h and then added H2O (20 mL). Extracted with EtOAc (3×20 mL) and the combined organic phases were concentrated in vacuo. Purified by flash chromatography on silica using EtOAc in heptane as eluent. The obtained compound was treated with TFA (2 mL) at rt for 1.5 h. The crude reaction mixture was added sat. Na2CO3 to pH=7 and the extracted with EtOAc (3×10 mL). The combined organic phases was washes with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The pure compound was obtained by flash chromatography on silica using EtOAc in heptane as eluent.

Workup

  1. extractionExtracted with EtOAc (3×20 mL)
  2. concentrationthe combined organic phases were concentrated in vacuo
  3. customPurified by flash chromatography on silica
  4. additionThe obtained compound was treated with TFA (2 mL) at rt for 1.5 h
  5. customThe crude reaction mixture
  6. extractionthe extracted with EtOAc (3×10 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe pure compound was obtained by flash chromatography on silica

Sources & evidence

ORD record
ord-00bd3cbd176a482592d072410d518ae1
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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