Dimethylformamide → HCID 59379928, compound

HRID 2353735Notes

Reaction equation

HRID 2353735 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([S:11]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])([CH3:10])[CH3:9])[CH:5]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[N:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>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.COCCOC.O>[CH:14]1([S:11]([C:8]([C:6]2[CH:5]=[C:4]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])[N:3]=[C:2]([C:34]3[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=3)[N:7]=2)([CH3:10])[CH3:9])(=[O:13])=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380062HCID 59380062, compound

Product 1

HCID 59379928HCID 59379928, compoundYield 79.9%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
95 °C

Procedure

Bis(triphenylphosphine)palladium(II) chloride (200 mg, 0.28 mmol) was added to 2-chloro-4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (1.66 g, 4.28 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.406 g, 6.42 mmol) and sodium carbonate (10 mL, 20.00 mmol) in a mixture of ethanol (5 mL), DMF (10 mL), water (7 mL) and DME (25 mL) at RT. The resulting mixture was degassed then stirred at 95° C. for 18 hours. The reaction mixture was allowed to cool and diluted with ethyl acetate (200 mL) then washed with water (2×150 mL), and brine (150 mL). The organic layer was dried (Na2SO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 10 to 60% ethyl acetate in isohexane, and the residue obtained was triturated with a mixture of diethyl ether and isohexane to give the desired material as a pale pink solid (1.52 g).

Workup

  1. customThe resulting mixture was degassed
  2. temperatureto cool
  3. additiondiluted with ethyl acetate (200 mL)
  4. washthen washed with water (2×150 mL), and brine (150 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford crude product
  9. customThe crude product was purified by flash silica chromatography, elution gradient 10 to 60% ethyl acetate in isohexane
  10. customthe residue obtained
  11. customwas triturated with a mixture of diethyl ether and isohexane

Sources & evidence

ORD record
ord-3cf04d6327ab468881715050fcc6bf51
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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