Ammonium Chloride → 4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 1685184Notes

Reaction equation

HRID 1685184 reaction equation
Br[C:2]1(Br)[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][C:3]1=[O:12].[Cl-].[NH4+].CO.C(Cl)Cl>C1COCC1.[Zn]>[Cl:11][C:9]1[C:10]2[CH2:2][C:3](=[O:12])[NH:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226129Dichloromethane methanolHCID 223909585,5-Dibromo-4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one

Product 1

HCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-oneYield 378.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add zinc (2 equiv; 12.12 mmol; 792 mg) to a suspension of 5,5-dibromo-4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (6.06 mmol; 1.98 g) in THF (20 mL) and add saturated ammonium chloride aqueous (3 mL) at 20° C. (exothermic). Stir 20 min then filter through Celite®, rinse with THF, wash the organic phase twice with saturated ammonium chloride. Extract combined aqueous layers four times with 100 mL 1:1 THF:EA, wash the combined organic phases with saturated ammonium chloride, dry over MgSO4, filter through silica gel plug, rinse with 1 L 5% MeOH/DCM and evaporate filtrates. Suspend crude solid in refluxing mixtures of DCM/EA and load onto 330 g of dry silica gel. Chromatograph with 0 to 2% MeOH/DCM to provide the title compound 3.89 g (22.93 mmol; 59%). MS (ES+): m/z=168 (M−H).

Workup

  1. filtrationthen filter through Celite®
  2. washrinse with THF
  3. washwash the organic phase twice with saturated ammonium chloride
  4. extractionExtract
  5. washEA, wash the combined organic phases with saturated ammonium chloride
  6. dry with materialdry over MgSO4
  7. filtrationfilter through silica gel plug
  8. washrinse with 1 L 5% MeOH/DCM
  9. customevaporate filtrates
  10. temperaturein refluxing mixtures of DCM/EA and load onto 330 g of dry silica gel

Sources & evidence

ORD record
ord-329a8faff77a44c5b7792c4128cea9c8
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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