Tetramethyltin → HCID 54511693, compound

HRID 2226105Notes

Reaction equation

HRID 2226105 reaction equation
Br[C:2]1[C:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[C:4]([F:26])[CH:3]=1.ClN1C(=O)CC[C:29]1=O.C[Sn](C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C(C)=CC=CC=1>[CH3:11][C:9]1([CH3:12])[O:8][C:7]2[C:2]([CH3:29])=[CH:3][C:4]([F:26])=[C:5]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[C:6]=2[O:10]1

Participants

6

Reactant 3

HCID 11661TetramethyltinHCID 31398ChlorosuccinimideHCID 18966276HCID 18966276, compound3×

Product 1

HCID 54511693HCID 54511693, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

Synthesis of this compound starts with 3-(7-bromo-2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-yl)-1-methyl-6-trifluoromethyluracil (Compound 17) which may be synthesized using the methods of Example 1, Steps F through H, by substituting N-bromosuccinimide for N-chlorosuccinimide in Step F. In a tube are placed 2.2 g (0.005 mole) of 3-(7-bromo-2,2-dimethyl-5-fluoro- 1,3-benzodioxol-4-yl)- 1 -methyl-6-trifluoromethyluracil, 0.95 g (0.0053 mole) of tetramethyl tin, 0.05 g (0.00005 mole) of tetrakis(triphenylphosphine)palladium(0), and 3 mL of xylene. The tube is sealed and heated at 120 ° C for approximately 20 hours after which it is cooled, the seal is broken, and the contents are removed. The reaction mixture is passed through a column of silica gel, eluting with heptane/ethyl acetate ( 1:1 ). The product-containing fractions are combined, and the solvent is evaporated under reduced pressure, yielding 3-(2,2-dimethyl-5-fluoro-7-methyl- 1,3-benzodioxol-4-yl)- 1 -methyl-6-trifluoromethyluracil as the residue.

Workup

  1. customSynthesis of this compound
  2. custommay be synthesized
  3. customIn a tube are placed
  4. customThe tube is sealed
  5. temperatureis cooled
  6. customthe contents are removed
  7. washeluting with heptane/ethyl acetate ( 1:1 )
  8. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-54f52b2f7fb14b88ac5bf1f369cbb2ac
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

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