Isopropyl iodide → 6-Bromo-8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2389969Notes

Reaction equation

HRID 2389969 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:16](=[O:17])[NH:15][C:7]2[N:8]=[C:9]([S:13][CH3:14])[N:10]=[C:11]([CH3:12])[C:6]=2[CH:5]=1.I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[Br:3][C:4]1[C:16](=[O:17])[N:15]([CH:19]([CH3:21])[CH3:20])[C:7]2[N:8]=[C:9]([S:13][CH3:14])[N:10]=[C:11]([CH3:12])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 592589096-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 592589536-Bromo-8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
46 °C

Procedure

To a suspension of NaH (120 mg, 5.00 mmol) in DMF (15 mL) was added 6-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (572 mg, 2 mmol). The mixture was heated to 46° C. The solution was cooled down slightly and 2-iodopropane (0.30 mL, 3.0 mmol) was added. The mixture was heated at 46° C. for 30 min and then cooled to room temperature and partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and concentrated. The crude product was purified by silica gel flash chromatography, using EtOAc/Hexane, to give the title compound (390 mg, 59%).

Workup

  1. temperatureThe solution was cooled down slightly
  2. temperatureThe mixture was heated at 46° C. for 30 min
  3. temperaturecooled to room temperature
  4. custompartitioned between water and ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-0742ec46b387422ca53ca4115c308c1c
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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