Hexane → 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrimidine

HRID 500712Notes

Reaction equation

HRID 500712 reaction equation
[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9](SC)[N:8]=2)=[CH:5][N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1.O[O:19][S:20]([O-:22])=O.[K+].[CH3:24]CCCCC.CCOC(C)=O>C1COCC1.O>[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:20]([CH3:24])(=[O:22])=[O:19])[N:8]=2)=[CH:5][N:4]([CH:15]([CH3:16])[CH3:17])[N:3]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl Acetate2×HCID 23707502Potassium hydroxy sulfiteHCID 594244094-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

Product 1

HCID 578563434-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrimidineYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine B-1-1 (15.5 g, 43 mmol) in THF (350 mL) and water (350 mL) was added oxone (39.6 g, 64.6 mmol) at 0-5° C. After the addition, the mixture was stirred at rt overnight. TLC (hexane:EtOAc=5:1) showed the reaction was complete, EtOAc (500 mL) was added. The organic layer was separated, washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated to give 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrimidine B-1-2 (16 g, 94.9%).

Workup

  1. additionAfter the addition
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eb2df6cd7b194c2886e8586bec06d20c
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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