Imidazole → 7-(1-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-YL)-2-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidine

HRID 82159Notes

Reaction equation

HRID 82159 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[C:18]([I:19])=[CH:17][N:16]([C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])[C:14]=2[N:15]=1.N1C=CN=C1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Si:1]([O:22][CH2:21][C:20]([N:16]1[C:14]2[N:15]=[C:10]([Cl:9])[N:11]=[CH:12][C:13]=2[C:18]([I:19])=[CH:17]1)([CH3:24])[CH3:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 866720852-(2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-ol

Product 1

HCID 866720847-(1-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-YL)-2-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidineYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyldimethylsilyl chloride (78.8 g, 518 mmol) was added to 2-(2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-ol (140 g, 398 mmol) (see Preparation 43) and imidazole (67.8 g, 996 mmol) in DMF (996 mL) at 0° C. The mixture was stirred at room temperature for 16 hours. The mixture was poured into saturated aqueous sodium bicarbonate (1500 mL) and extracted with heptane:EtOAc (1:1, 1500 mL). The organic extract was washed with brine (2×900 mL) then dried over magnesium sulfate and evaporated in vacuo to afford the title compound as a brown gum in 96% yield, 178.2 g.

Workup

  1. extractionextracted with heptane:EtOAc (1:1, 1500 mL)
  2. extractionThe organic extract
  3. washwas washed with brine (2×900 mL)
  4. dry with materialthen dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b96afca95b8f42eaaad18db95e6b706f
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…