Methanol → HCID 59128639, compound

HRID 1991005Notes

Reaction equation

HRID 1991005 reaction equation
[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[C:24](=[O:25])[N:23]([CH3:26])[C:16]4[N:17]=[C:18](SC)[N:19]=[CH:20][C:15]=4[CH:14]=3)[CH:7]=2)[CH2:3][CH2:2]1.O[O:29][S:30]([O-:32])=O.[K+].[CH3:34]O>C1COCC1.O>[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[C:24](=[O:25])[N:23]([CH3:26])[C:16]4[N:17]=[C:18]([S:30]([CH3:34])(=[O:32])=[O:29])[N:19]=[CH:20][C:15]=4[CH:14]=3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 59128627HCID 59128627, compound

Product 1

HCID 59128639HCID 59128639, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Cyclopropyl-4-methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzamide (21 mg) was dissolved in a mixture of 2 mL MeOH, 1 mL THF and 1 mL water. OXONE™ (1.63 mg, 0.09 mmol) was added, and the reaction mixture was stirred for three hours at room temperature. The reaction mixture was then partitioned between water and EtOAc, and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 25 mg of N-cyclopropyl-3-(2-methanesulfonyl-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-4-methyl-benzamide.

Workup

  1. customThe reaction mixture was then partitioned between water and EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fbc1cb7b1dc94e60a42d105121ff833b
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

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