Sodium hydride → HCID 59489502, compound

HRID 2361513Notes

Reaction equation

HRID 2361513 reaction equation
[N:1]1[C:2]2[N:3]([C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1.[H-].[Na+].[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([O:40][CH2:41][CH2:42][CH2:43]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:39])=[O:38])=[CH:33][CH:32]=1>CN(C=O)C>[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([O:40][CH2:41][CH2:42][CH2:43][N:13]([C:10]2[CH:9]=[CH:8][C:7]([C:4]3[N:3]4[C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=5[N:23]=[C:2]4[N:1]=[CH:6][CH:5]=3)=[CH:12][CH:11]=2)[C:14]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:20])(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2303703-(4-Methylphenyl)sulfonyloxypropyl 4-methylbenzenesulfonateHCID 58362335HCID 58362335, compound

Product 1

HCID 59489502HCID 59489502, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (4-(benzo[4,5]imidazo[1,2-a]pyrimidin-4-yl)phenyl)carbamate (300 mg, 0.83 mmol) in DMF (9 mL) at 0° C. was added NaH (38 mg, 0.91 mmol, 60% dispersed in oil). After stirring for 5 min at 0° C. for 5 min, ice bath was removed and reaction was stirred at rt for 20 min. The reaction was cooled again at 0° C. and propane-1,3-diyl bis(4-methylbenzenesulfonate) (653 mg, 1.7 mmol) was added in 6 portions. After stirring at 0° C. for 5 min, the reaction was let stir at rt for 2 h and quenched with saturated NH4Cl solution (40 mL). The mixture was extracted with DCM (3×30 mL). The combined organic phase was washed with water (2×50 mL) and dried over MgSO4 and concentrated. The residue was first purified by silica chromatography (THF in DCM, 0% to 18%) and then reversed phase HPLC (TFA buffered water/MeCN) to afford the title compound as an orange solid (160 mg, 34%). MS (ESI) m/z [M+H]+573.

Workup

  1. customice bath was removed
  2. customreaction
  3. stirringwas stirred at rt for 20 min
  4. temperatureThe reaction was cooled again at 0° C.
  5. stirringAfter stirring at 0° C. for 5 min
  6. stirringthe reaction was let stir at rt for 2 h
  7. customquenched with saturated NH4Cl solution (40 mL)
  8. extractionThe mixture was extracted with DCM (3×30 mL)
  9. washThe combined organic phase was washed with water (2×50 mL)
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated
  12. customThe residue was first purified by silica chromatography (THF in DCM, 0% to 18%)

Sources & evidence

ORD record
ord-8fafbff79bb84d6986c42d5ef98da278
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

Loading…