Water → HCID 86665993, compound

HRID 530083Notes

Reaction equation

HRID 530083 reaction equation
[C:1]([Si:5]([NH:8][C:9]1[N:10]=[C:11]([Cl:18])[C:12]2[CH:17]=[CH:16][NH:15][C:13]=2[N:14]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].CI.[C:21]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Si:5]([NH:8][C:9]1[N:10]=[C:11]([Cl:18])[C:12]2[CH:17]=[CH:16][N:15]([CH3:21])[C:13]=2[N:14]=1)([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22921992HCID 22921992, compound

Product 1

HCID 86665993HCID 86665993, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(t-Butyl-dimethyl silyl)amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CXXII) (700 mg, 2.5 mmol), 0.18 mL (3.5 mmol) of methyl iodide in DMF (10 mL), and K2CO3 (552 mg, 4 mmol) were reacted at ambient temperature for 15 h. After addition of H2O (10 mL), the reaction was extracted with EtOAc (100 mL), and the organic layer was washed with a brine solution (10 mL), and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by flash column chromatography (PE/EtOAc=10/1 to 5/1) to afford 2-(t-butyl-dimethylsilyl)amino-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (CXXIII) (750 mg, 100%) as a light yellow oil. LCMS (ESI) m/z=297 (M+H)+.

Workup

  1. extractionthe reaction was extracted with EtOAc (100 mL)
  2. washthe organic layer was washed with a brine solution (10 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by flash column chromatography (PE/EtOAc=10/1 to 5/1)

Sources & evidence

ORD record
ord-cfb16c83bdb24526bb4bebf65cf9a6b4
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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