Sodium Carbonate → HCID 86688548, compound

HRID 710551Notes

Reaction equation

HRID 710551 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([NH:9][C:10]([N:12]3[CH2:17][CH2:16][C:15](=[CH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[CH2:14][CH2:13]3)=[O:11])[S:8][C:4]=2[CH:3]=1.[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>CN(C=O)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>[N:27]1[CH:32]=[C:31]([C:2]2[CH:26]=[CH:25][C:5]3[N:6]=[C:7]([NH:9][C:10]([N:12]4[CH2:17][CH2:16][C:15](=[CH:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=5)[CH2:14][CH2:13]4)=[O:11])[S:8][C:4]=3[CH:3]=2)[CH:30]=[N:29][CH:28]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86688544HCID 86688544, compound

Product 1

HCID 86688548HCID 86688548, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The compound (400 mg, 932 μmol) obtained in Example 1 and pyrimidine-5-boronic acid (289 mg, 2.33 mmol) were dissolved in DMF (10 mL), and a 2N sodium carbonate aqueous solution (1.62 mL, 3.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (107 mg, 93.2 μmol) were added thereto. The resulting mixture was subjected to reaction at 120° C. for 40 minutes in a microwave reactor. A saturated ammonium chloride aqueous solution was added to the resulting mixture to stop the reaction, and after extraction with ethyl acetate, the extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the residue obtained by evaporation under reduced pressure was purified using medium pressure flash column chromatography (silica gel; methanol:chloroform=1:40), thereby giving the title compound (160 mg, 40%) as a pale brown solid.

Workup

  1. customThe resulting mixture was subjected to reaction at 120° C. for 40 minutes in a microwave reactor
  2. customthe reaction
  3. extractionafter extraction with ethyl acetate
  4. washthe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. customthe residue obtained by evaporation under reduced pressure
  8. customwas purified

Sources & evidence

ORD record
ord-de65856ca1824b7b9950a60eab4e36ff
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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