Sodium Carbonate → HCID 59380168, compound

HRID 2353732Notes

Reaction equation

HRID 2353732 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])([CH3:10])[CH3:9])[CH:5]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]2[CH3:22])[N:3]=1.CC1(C)C(C)(C)OB([C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.O.C(O)C.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>[CH2:14]([S:11]([C:8]([C:6]1[CH:5]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]2[CH3:22])[N:3]=[C:2]([C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)[N:7]=1)([CH3:10])[CH3:9])(=[O:13])=[O:12])[CH3:15]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380053HCID 59380053, compound

Product 1

HCID 59380168HCID 59380168, compoundYield 57.8%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
85 °C

Procedure

Dichlorobis(triphenylphosphine)palladium(II) (0.360 g, 0.51 mmol) was added to a degassed solution of 2-chloro-4-(2-ethylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (1.784 g, 5.13 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.404 g, 6.41 mmol) and sodium carbonate (12.82 mL, 25.64 mmol) in a mixture of 18% DMF in DME:water:ethanol (7:3:2) (25 mL). The resulting solution was stirred at 85° C. for 2 hours. The reaction mixture was concentrated and partitioned between DCM (150 mL), and water (100 mL) and the organics washed with brine (100 mL), dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 2.5% methanol in DCM, to give the desired material as a brown solid (1.20 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between DCM (150 mL), and water (100 mL)
  3. washthe organics washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 2.5% methanol in DCM

Sources & evidence

ORD record
ord-6ce6fb3f6da84816b2451ba15e5a3e72
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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