Ethanol → HCID 59380069, compound

HRID 2353758Notes

Reaction equation

HRID 2353758 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[CH:12]=[C:11]([C:22]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:27])=[O:26])([CH3:24])[CH3:23])[N:10]=1.C(O)C.CN(C=O)C>COCCOC.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.O>[CH3:21][C@H:16]1[CH2:17][O:18][CH2:19][CH2:20][N:15]1[C:13]1[CH:12]=[C:11]([C:22]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:27])=[O:26])([CH3:24])[CH3:23])[N:10]=[C:9]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[N:14]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 6115AnilineHCID 6228DimethylformamideHCID 59380219HCID 59380219, compound

Product 1

HCID 59380069HCID 59380069, compoundYield 75.6%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.773 g, 3.53 mmol) and 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(2-pyridin-2-ylsulfonylpropan-2-yl)pyrimidine (1.4 g, 3.53 mmol) were suspended in a mixture of DME (10 mL), ethanol (10.00 mL), DMF (10.00 mL) and water (10 mL) at RT under nitrogen. The mixture was purged with nitrogen and bis(triphenylphosphine)palladium(II) chloride (0.124 g, 0.18 mmol) was added. The resulting suspension was stirred at 80° C. for 90 minutes under an atmosphere of nitrogen. The reaction mixture was concentrated and diluted with ethyl acetate (150 mL), and washed with water (2×150 mL) and saturated brine (100 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford the crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in DCM, to give the desired material as a yellow foam (1.210 g).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate (150 mL)
  4. washwashed with water (2×150 mL) and saturated brine (100 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product
  9. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in DCM

Sources & evidence

ORD record
ord-c7e84b8e633b446dbafe54f7c4f3f3a6
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…