Tetrahydrofuran → HCID 178504840, compound

HRID 982610Notes

Reaction equation

HRID 982610 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:19]([OH:20])=[N:18][C:11]2[N:12]=[C:13](SC)[N:14]=[CH:15][C:10]=2[CH:9]=1.O[O:22][S:23]([O-:25])=O.[K+].O1CCC[CH2:28]1>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:19]([OH:20])=[N:18][C:11]2[N:12]=[C:13]([S:23]([CH3:28])(=[O:25])=[O:22])[N:14]=[CH:15][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 178503379HCID 178503379, compound

Product 1

HCID 178504840HCID 178504840, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-(2-chlorophenyl)-2-methylthio-pyrido[2,3-d]pyrimidin-7-ol (25.2 g, 82.9 mmol) in 700 mL of tetrahydrofuran was added a slurry of Oxone™ (105 g, 171 mmol) in 200 mL of water. The reaction mixture was stirred for 5 hours, filtered, then concentrated in vacuo. The resulting slurry was filtered and the collected solid was washed with water and dried to give 23.2 g (83%) of 6-(2-chlorophenyl)-2-methanesulfonyl-pyrido[2,3-d]pyrimidin-7-ol (Sulfone 2) as a light-yellow solid. (mass spec. M+H+=336, mp=215.1-221.1° C.).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. filtrationThe resulting slurry was filtered
  4. washthe collected solid was washed with water
  5. customdried

Sources & evidence

ORD record
ord-666760ac980848e2b689ecdd7833458e
Source dataset
uspto-grants-2005_03
Patent number
US06861423B2

Reaction notes

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