1,2-Dimethoxyethane → HCID 59379878, compound

HRID 2353706Notes

Reaction equation

HRID 2353706 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>CN(C=O)C.C(OCC)(=O)C.O.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.C(O)C>[CH3:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]1[CH:5]=[C:4]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=[C:2]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[N:7]=1

Participants

10

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59379906HCID 59379906, compound

Product 1

HCID 59379878HCID 59379878, compoundYield 95.9%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

trans-Dichlorobis(triphenylphosphine)palladium (II) (0.039 g, 0.06 mmol) was added to a mixture of 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidine (0.411 g, 1.11 mmol), 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.366 g, 1.67 mmol) and sodium carbonate (0.233 mL, 5.56 mmol) in 18% DMF in a mixture of 7:3:2 DME:water:ethanol (100 mL) at RT under nitrogen. The resulting solution was stirred at 90° C. for 5 hours. The reaction was cooled and diluted with ethyl acetate and water. The reaction mixture was extracted with ethyl acetate and the combined organics dried (MgSO4), filtered and evaporated. The crude product was chromatographed on silica, eluting with 0-5% methanol in DCM, to give the desired material as a white solid (0.453 g).

Workup

  1. customat RT
  2. temperatureThe reaction was cooled
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialthe combined organics dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed on silica
  8. washeluting with 0-5% methanol in DCM

Sources & evidence

ORD record
ord-192c0e81379c4171a741b754726f28da
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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