Ammonium Chloride → HCID 86667333, compound

HRID 334114Notes

Reaction equation

HRID 334114 reaction equation
Br[C:2]1(Br)[C:6]2[N:7]=[C:8]([Cl:17])[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]=2[N:4]([CH3:18])[C:3]1=[O:19].[Cl-].[NH4+]>C1COCC1.C(Cl)Cl.[Zn]>[Cl:17][C:8]1[N:9]=[C:10]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:5]2[N:4]([CH3:18])[C:3](=[O:19])[CH2:2][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86667334HCID 86667334, compound

Product 1

HCID 86667333HCID 86667333, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 7,7-dibromo-2-chloro-5-methyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one (1.70 g, 3.99 mmol) in 2M aqueous ammonium chloride solution (9.96 mL, 19.9 mmol) and THF (40 mL) at 0° C. was added zinc dust (573.4 mg, 8.775 mmol). The reaction mixture was stirred at RT for 30 min and then diluted with DCM (40 mL). The reaction mixture was filtered through a pad of Celite. The layers were separated, and the organic layer was washed with saturated aqueous NaHCO3 solution, water, and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 679 mg (63.4%) of 2-chloro-5-methyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one a solid. MS(ESI) m/z: 269.2 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated aqueous NaHCO3 solution, water, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-083824b6a6324271a431c556cfe8017d
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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