2,6-Lutidine → HCID 59224637, compound

HRID 1811717Notes

Reaction equation

HRID 1811717 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=2[CH3:14])[CH:5]=[C:4]([Cl:16])[N:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])(=O)=O>ClCCl>[Si:31]([O:15][C:10]1[CH:11]=[CH:12][C:13]([CH3:14])=[C:8]([C:6]2[CH:5]=[C:4]([Cl:16])[N:3]=[C:2]([NH2:1])[N:7]=2)[CH:9]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 59224693HCID 59224693, compound

Product 1

HCID 59224637HCID 59224637, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(2-amino-6-chloropyrimidin-4-yl)-4-methylphenol (2.12 g, 9.00 mmol) obtained in Step 4 above was placed in a reaction vessel, and then dichloromethane (60 ml) was added thereto. The mixture was cooled to 0° C. 2,6-Lutidine (1.25 ml, 10.7 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (2.27 ml, 9.88 mmol) were sequentially added to the solution. The mixture was stirred at 0° C. for 1 hour and then at room temperature for 30 minutes. The resulting reaction solution was diluted with dichloromethane (150 ml), and sequentially washed with a saturated aqueous sodium bicarbonate solution (150 ml), water (150 ml), and a saturated aqueous sodium chloride solution (150 ml). The dichloromethane solution was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=9:1 to 6:1) to yield 4-[5-(tert-butyldimethylsilanyloxy)-2-methylphenyl]-6-chloropyrimidin-2-ylamine (Compound 1-5) (2.41 g, 77%).

Workup

  1. waitat room temperature for 30 minutes
  2. customThe resulting reaction solution
  3. washsequentially washed with a saturated aqueous sodium bicarbonate solution (150 ml), water (150 ml)
  4. dry with materialThe dichloromethane solution was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=9:1 to 6:1)

Sources & evidence

ORD record
ord-8fdf159e020d497bacbb9efdada6862b
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

Loading…