Toluene-4-sulfonic acid 2-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-hydroxy-2-hydroxymethyl-propyl ester → HCID 71743018, compound

HRID 82250Notes

Reaction equation

HRID 82250 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C:11]([CH2:26][OH:27])([CH2:24]O)[CH2:12][O:13]S(C3C=CC(C)=CC=3)(=O)=O)[C:4]=2[N:5]=[CH:6][N:7]=1>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C:11]3([CH2:12][OH:13])[CH2:24][O:27][CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 1

HCID 86672115Toluene-4-sulfonic acid 2-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-hydroxy-2-hydroxymethyl-propyl ester

Product 1

HCID 71743018HCID 71743018, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

nButyllithium (12.2 mL, 30.6 mmol, 2.5 M in hexanes) was added to toluene-4-sulfonic acid 2-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-hydroxy-2-hydroxymethyl-propyl ester (Preparation 210, 5.73 g, 13.9 mmol) in THF (100 mL) at 0° C. and stirred for 5 min. The reaction mixture was then warmed to room temperature and stirred for 16 hours, at which point it was quenched with saturated aqueous ammonium chloride. The resulting mixture was extracted with ethyl acetate (100 mL×3) and the combined organic phases were dried (MgSO4) and concentrated in vacuo. The crude product was triturated with dichloromethane and filtered to afford the title compound in 36% yield, 1.2 g.

Workup

  1. stirringstirred for 16 hours, at which point it
  2. customwas quenched with saturated aqueous ammonium chloride
  3. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×3)
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was triturated with dichloromethane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f46eaa32559d48ea8612b368bc4c92c8
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…