Water → HCID 86641357, compound

HRID 1693331Notes

Reaction equation

HRID 1693331 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[CH2:15][S:14][N:13]=[C:12]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]3=[N:32][N:33]([CH2:35][C:36]4[C:41]([CH3:42])=[C:40]([O:43][CH3:44])[C:39]([CH3:45])=[CH:38][N:37]=4)[N:34]=[C:9]([C:10]=23)[CH:8]=1)(=O)=O.[N:48]1[CH:53]=[C:52](B(O)O)[CH:51]=[N:50][CH:49]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:44][O:43][C:40]1[C:39]([CH3:45])=[CH:38][N:37]=[C:36]([CH2:35][N:33]2[N:34]=[C:9]3[CH:8]=[C:7]([C:52]4[CH:53]=[N:48][CH:49]=[N:50][CH:51]=4)[C:16]4[CH2:15][S:14][N:13]=[C:12]([N:17]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[C:11]([C:10]=43)=[N:32]2)[C:41]=1[CH3:42]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86641355HCID 86641355, compound

Product 1

HCID 86641357HCID 86641357, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

4-[Bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl trifluoromethanesulfonate (50 mg) was dissolved in 1,4-dioxane (4 ml). Pyrimidine-5-boronic acid (13 mg), a 2 N sodium carbonate solution (2 ml) and bis(triphenylphosphine)palladium (II) dichloride (5 mg) were added and the mixture was stirred at 40° C. for two hours. Water was placed into the reaction solution, followed by extraction with ethyl acetate. The resulting organic layer was sequentially washed with water and brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound as an oil (45 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resulting organic layer was sequentially washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-29959d1cea304b5ca4de7d3bc46b9693
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

Loading…