Water → HCID 86665994, compound

HRID 530086Notes

Reaction equation

HRID 530086 reaction equation
[Si:1]([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)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[CH:20]([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Si:1]([NH:8][C:9]1[N:10]=[C:11]([Cl:18])[C:12]2[CH:17]=[CH:16][N:15]([CH:20]([CH3:22])[CH3:21])[C:13]=2[N:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 22921992HCID 22921992, compound

Product 1

HCID 86665994HCID 86665994, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(t-Butyl-dimethylsilanyl)amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CXXII) (5 g, 17.7 mmol), 2-iodopropane (4.5 g, 26.6 mmol) and K2CO3 (4.3 g, 26.6 mmol) in DMF (20 mL) were reacted at ambient temperature for 15 h. After addition of H2O (50 mL) to the reaction mixture, the aqueous solution was extracted with EtOAc (300 mL) and the organic layer was washed with a brine solution (50 mL) and dried with Na2SO4. The solvents were removed in vacuo and the residue was purified by flash column chromatography (pet ether/EtOAc=10/1 to 5/1) to afford 2-(t-butyl-dimethylsilyl)amino-4-chloro-7-i-propyl-pyrrolo[2,3-d]pyrimidine (CXXXIII, 5.7 g, 100%) as a light yellow oil. LCMS: (ESI) m/z=325 (M+H)+.

Workup

  1. extractionthe aqueous solution was extracted with EtOAc (300 mL)
  2. washthe organic layer was washed with a brine solution (50 mL)
  3. dry with materialdried with Na2SO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by flash column chromatography (pet ether/EtOAc=10/1 to 5/1)

Sources & evidence

ORD record
ord-8efff0b652fd4104a9ed1671a55d49fc
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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