Methanol → (2-methylsulfonyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine

HRID 491369Notes

Reaction equation

HRID 491369 reaction equation
CS[C:3]1[N:8]=[C:7]([NH:9][C:10]2[NH:11][N:12]=[C:13]([CH3:15])[CH:14]=2)[CH:6]=[C:5]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:4]=1.O[O:23][S:24]([O-:26])=O.[K+].[CH3:28]O>O>[CH3:28][S:24]([C:3]1[N:8]=[C:7]([NH:9][C:10]2[NH:11][N:12]=[C:13]([CH3:15])[CH:14]=2)[CH:6]=[C:5]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:4]=1)(=[O:26])=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 178419055[2-methylsulfanyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine

Product 1

HCID 178419103(2-methylsulfonyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of the above-prepared [2-methylsulfanyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (500 mg, 1.63 mmol) in MeOH (10 mL) is added a solution of oxone (3.0 g) in water (10 mL). The reaction mixture is stirred at room temperature for 15 hours and most of the solvent is evaporated. The residue is partitioned between DCM and aqueous saturated NaHCO3. The organic layer is washed with brine, dried, filtered and evaporated. The residue is triturated in MeOH and the resulting white solid is collected by filtration to give [2-methylsulfonyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

Workup

  1. customis evaporated
  2. customThe residue is partitioned between DCM and aqueous saturated NaHCO3
  3. washThe organic layer is washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is triturated in MeOH
  8. filtrationthe resulting white solid is collected by filtration

Sources & evidence

ORD record
ord-b86e4756b5dc48ec84a02c3616df6920
Source dataset
uspto-grants-2009_05
Patent number
US07531536B2

Reaction notes

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