Sodium Carbonate → HCID 59379933, compound

HRID 2353743Notes

Reaction equation

HRID 2353743 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]([C:15]([S:18]([C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:20])=[O:19])([CH3:17])[CH3:16])[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+]>CN(C=O)C.COCCOC.C(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>[CH3:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]1[CH:5]=[C:4]([C:15]([S:18]([C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:20])=[O:19])([CH3:17])[CH3:16])[N:3]=[C:2]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[N:7]=1

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59379971HCID 59379971, compound

Product 1

HCID 59379933HCID 59379933, compoundYield 93.9%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Dichlorobis(triphenylphosphine)-palladium(II) (0.103 g, 0.15 mmol) was added to 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(2-tert-butylsulfonylpropan-2-yl)pyrimidine (1.10 g, 2.93 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.833 g, 3.80 mmol) and 2M aqueous sodium carbonate (5.27 mL, 10.53 mmol) in DMF (6 mL), DME (5 mL), ethanol (5 mL) and water (12.5 mL) at RT under nitrogen. The reaction was purged with nitrogen for 15 minutes and the resulting mixture was stirred at 80° C. for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic solution was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was chromatographed on silica, eluting with 25%-100% ethyl acetate in isohexane, to give the desired material as a yellow solid (1.19 g).

Workup

  1. customThe reaction was purged with nitrogen for 15 minutes
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica
  8. washeluting with 25%-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-7ec6242bfd264e0a9894382e308d779d
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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