Sodium Bicarbonate → tert-butyl 2-(4-([3-chloro-4-(3-chlorophenoxy)phenyl)amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethylcarbamate

HRID 1926102Notes

Reaction equation

HRID 1926102 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)[NH2:25].C(=O)([O-])O.[Na+]>C(O)(C)C>[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:2]2[C:3]3[N:10]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:26]=[CH:27][C:28]=1[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 176055343-Chloro-4-(3-chlorophenoxy)anilineHCID 56851233tert-butyl 2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethylcarbamate

Product 1

HCID 67520372tert-butyl 2-(4-([3-chloro-4-(3-chlorophenoxy)phenyl)amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethylcarbamateYield 81.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethylcarbamate (1.19 g), 3-chloro-4-(3-chlorophenoxy)aniline (1.22 g) and isopropyl alcohol (12.0 mL) was stirred at 80° C. for 15 hrs. Under ice-cooling, aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=50/50→100/0), and washed with diisopropyl ether-hexane to give the title compound (1.69 g) as crystals.

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=50/50→100/0)
  7. washwashed with diisopropyl ether-hexane

Sources & evidence

ORD record
ord-57d2275529344830ba8a2127878c22cb
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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