Isopropyl iodide → 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

HRID 500711Notes

Reaction equation

HRID 500711 reaction equation
[I:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1.I[CH:16]([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+].CCCCCC>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)=[CH:4][N:5]([CH:16]([CH3:18])[CH3:17])[N:6]=1

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 8058HexaneHCID 11430Potassium CarbonateHCID 468641604-(5-Iodo-1H-pyrazol-4-yl)-2-(methylsulfanyl)pyrimidine

Product 1

HCID 594244094-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylthio)pyrimidineYield 47.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(5-iodo-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine (A) (31.8 g, 0.1 mol), 2-iodo-propane (85 g, 50 mL, 0.5 mol) and K2CO3 (16.5 g, 0.12 mol) in DMF (500 mL) was heated at 40˜50° C. overnight. When TLC (hexane: EtOAc=15:1) showed the reaction was complete, DMF was evaporated under reduced pressure. The residue was taken up with EtOAc (400 mL). The mixture was washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated to give crude product, which was purified via prep. HPLC to give pure 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine B-1-1 (17 g, 47.2%) as a yellow oil.

Workup

  1. temperaturewas heated at 40˜50° C. overnight
  2. customDMF was evaporated under reduced pressure
  3. washThe mixture was washed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified via prep

Sources & evidence

ORD record
ord-78b3fc8fdc9c418a8074fbf09cc9a9a1
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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