tert-Butyl methyl ether → HCID 117821294, compound

HRID 59130Notes

Reaction equation

HRID 59130 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[C:4](Cl)[N:3]=1.C([Sn](CCCC)(CCCC)[C:16]([O:18][CH2:19][CH3:20])=[CH2:17])CCC.[F-].[K+].CC(OC)(C)C>CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[C:4]([C:16]([O:18][CH2:19][CH3:20])=[CH2:17])[N:3]=1

Participants

8

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 2327892,4,6-Trichloro-5-methylpyrimidineHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 117821294HCID 117821294, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2,4,6-Trichloro-5-methylpyrimidine (2.0 g, 10.13 mmol) and bis(triphenylphosphine)palladium chloride (0.142 g, 0.20 mmol) in DMF (40 mL) was degased. Tributyl(1-ethoxyvinyl)stannane (3.59 mL, 10.64 mmol) was added. The mixture was heated at 100° C. for 1.5 h under nitrogen atmosphere. The mixture was poured into a solution of KF (6 g) in water (100 mL). MTBE (100 mL) was added mixture was for stirred 10 min. The solid was removed by filtration and was washed with MTBE (60 mL). The organic phase was washed with water, dried over sodium sulfate and evaporated. The mixture was purified by column chromatography eluting with DCM to give the title compound as a solid, 1.15 g (49%).

Workup

  1. customThe solid was removed by filtration
  2. washwas washed with MTBE (60 mL)
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe mixture was purified by column chromatography
  7. washeluting with DCM

Sources & evidence

ORD record
ord-e894754458d64daaa3880223b42daf44
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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