Sodium Sulfite → HCID 86667336, compound

HRID 334116Notes

Reaction equation

HRID 334116 reaction equation
[CH2:1]([C:4]1([CH3:22])[C:8]2[N:9]=[C:10]([Cl:19])[N:11]=[C:12]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:7]=2[N:6]([CH3:20])[C:5]1=[O:21])[CH:2]=C.C[N+]1([O-])CC[O:27]CC1.S([O-])([O-])=O.[Na+].[Na+].I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O.C(O)CCC>[Cl:19][C:10]1[N:11]=[C:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:7]2[N:6]([CH3:20])[C:5](=[O:21])[C:4]([CH2:1][CH:2]=[O:27])([CH3:22])[C:8]=2[N:9]=1

Participants

10

Reactant 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 86667335HCID 86667335, compound

Product 1

HCID 86667336HCID 86667336, compoundYield 99%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 2631-ButanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 7-allyl-2-chloro-5,7-dimethyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one (80.0 mg, 0.25 mmol) in anhydrous THF (3.0 m) and water (1.0 mL) cooled to 0° C. was added N-methylmorpholine N-oxide (34.8 mg, 0.29 mmol), followed by 2.5% osmium tetraoxide in tent-butanol. (0.033 mL, 0.025 mmol). The reaction mixture was stirred at ambient temperature under N2 for 16 h. Sodium sulfite (312.4 mg, 2.48 mmol) was then added, and the reaction mixture was stirred at RT for 20 min. The reaction mixture was diluted with water and then extracted with ethyl acetate (2×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude intermediate was then diluted with anhydrous THF (3.0 mL) and water (1.0). Sodium periodate (79.5 mg, 0.372 mmol) was added, and the reaction mixture was sonicated for 1 minute and then stirred at RT for 2 days. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 80.4 mg (99%) of 2-(2-chloro-5,7-dimethyl-4-morpholino-6-oxo-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)acetaldehyde. MS(ESI) m/z: 325.1 [M+1]−.

Workup

  1. stirringthe reaction mixture was stirred at RT for 20 min
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionThe crude intermediate was then diluted with anhydrous THF (3.0 mL) and water (1.0)
  7. customthe reaction mixture was sonicated for 1 minute
  8. stirringstirred at RT for 2 days
  9. washthe organic layer was washed with water and brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76a7a86acdc841809a193a873326dc3d
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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