Potassium hydroxy sulfite → HCID 86651597, compound

HRID 2386279Notes

Reaction equation

HRID 2386279 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[CH2:17][CH2:16]S[CH2:14][CH2:13]3)[C:7](=[O:18])[C:6]3([CH3:23])[CH2:19][O:20][CH2:21][CH2:22][N:5]3[C:4]=2[N:3]=1.O[O:25][S:26]([O-:28])=O.[K+]>CO.O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[CH2:13][CH2:14][S:26](=[O:28])(=[O:25])[CH2:16][CH2:17]3)[C:7](=[O:18])[C:6]3([CH3:23])[CH2:19][O:20][CH2:21][CH2:22][N:5]3[C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86651596HCID 86651596, compound

Product 1

HCID 86651597HCID 86651597, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-6a-methyl-5-(tetrahydro-2H-thiopyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (9.4 mg, 0.026 mmol) in MeOH (1 ml) at 0° C. was added dropwise a solution of oxone (40.7 mg, 0.066 mmol) in water (1 ml), and the reaction mixture was stirred at room temperature for 16 h, followed by solvent removal in vacuo. The residue was partitioned between EtOAc and water. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were dried and concentrated in vacuo to give 2-chloro-5-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-6a-methyl-6a,7,9,10-tetrahydro[1,4]oxazino[3,4-h]pteridin-6(5H)-one (6.5 mg, 0.017 mmol, 63% yield) as a white solid. This was used in the next step without further purification. MS [M+H] found 387.

Workup

  1. customfollowed by solvent removal in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. customThe combined organic phases were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-589639eae2784a51bb8a040ddf2d8917
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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