Chloroform → HCID 59655769, compound

HRID 2054361Notes

Reaction equation

HRID 2054361 reaction equation
I[C:2]1[C:3]2[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[N:22][C:4]=2[N:5]2[C:10]=1[CH:9]=[CH:8][N:7]=[C:6]2[NH:11][S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[SnH3]C1N=CC=CN=1.C(Cl)(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Li+].[Cl-]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[CH3:27][O:26][C:25]1[C:3]2[CH:2]=[C:10]3[CH:9]=[CH:8][N:7]=[C:6]([NH:11][S:12]([C:15]4[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=4)(=[O:14])=[O:13])[N:5]3[C:4]=2[N:22]=[CH:23][CH:24]=1

Participants

9

Reactant 5

HCID 6212ChloroformHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 11443305HCID 11443305, compoundHCID 871506562-Stannyl pyrimidine

Product 1

HCID 59655769HCID 59655769, compoundYield 29.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 24b (295 mg, 0.60 mmol), 27 (258 mg, 0.9 mmol), Pd2(dba)3.CHCl3 (120 mg, 0.12 mmol), PPh3 (60 mg, 0.24 mmol), LiCl (74 mg, 1.8 mmol) and CuI (23 mg, 0.12 mmol) in dioxane (25 mL) was refluxed for one hour. The solvent was evaporated and the crude dissolved in CH2Cl2. The organic solution was extracted three times with 4N HCl solution. The aqueous solutions were basified together with solid NaHCO3 and extracted with CH2Cl2. The organic solution was evaporated and the mixture was purified by flash column chromatography. Elution with CH2Cl2/MeOH (99/1) gave 23b (66 mg, 28%) and with CH2Cl2/MeOH (9/1) gave 25 (209 mg, 71%) as a yellow solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude dissolved in CH2Cl2
  3. extractionThe organic solution was extracted three times with 4N HCl solution
  4. extractionextracted with CH2Cl2
  5. customThe organic solution was evaporated
  6. customthe mixture was purified by flash column chromatography
  7. washElution with CH2Cl2/MeOH (99/1)

Sources & evidence

ORD record
ord-3e5ff65489a640578fdb71fd89672375
Source dataset
uspto-grants-2008_02
Patent number
US07329666B2

Reaction notes

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