Isopropanol → HCID 86603153, compound

HRID 736339Notes

Reaction equation

HRID 736339 reaction equation
[Li]CCCC.Br[C:7]1[C:15]2[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=2[N:9]([Si](C(C)C)(C(C)C)C(C)C)[CH:8]=1.[Br:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=1)[C:33](Cl)=[O:34].CC(O)C>CCOCC>[Br:27][C:28]1[CH:36]=[C:32]([C:33]([C:7]2[C:15]3[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=3[NH:9][CH:8]=2)=[O:34])[CH:31]=[N:30][CH:29]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 27812235-Bromonicotinoyl chlorideHCID 77520043HCID 77520043, compoundHCID 178418339Butyllithium

Product 1

HCID 86603153HCID 86603153, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-BuLi (11.3 mL, 2.5 M in Hexane, 28.3 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine (10.0 g, 25.7 mmol) in Et2O (250 mL) at −78° C. and stirred for 0.5 h. 5-Bromo-nicotinoyl chloride (6.8 g, 30.8 mmol) was added to the reaction mixture slowly and stirred for 3 h, warmed to room temperature, and stirred for an additional 12 h. The reaction mixture was quenched with saturated aqueous NH4Cl (150 mL) and stirred for 30 min. The aqueous layer was extracted with EtOAc (3×150 mL) and the combined organic layers were washed with brine (300 mL), dried (Na2SO4), filtered, and concentrated in vacuo to provide a crude solid. Trituration with 2-propanol provided the title compound as a pure white solid (7.5 g, 86%). MS: 337.5/339.5 (MH+); HPLC Rf: 4.02 min. (HPLC method 4).

Workup

  1. stirringstirred for 3 h
  2. stirringstirred for an additional 12 h
  3. customThe reaction mixture was quenched with saturated aqueous NH4Cl (150 mL)
  4. stirringstirred for 30 min
  5. extractionThe aqueous layer was extracted with EtOAc (3×150 mL)
  6. washthe combined organic layers were washed with brine (300 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide a crude solid

Sources & evidence

ORD record
ord-0e8d2246b0cb41c58785ba6b6a80ec8c
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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