Sodium Carbonate → HCID 59380031, compound

HRID 2353717Notes

Reaction equation

HRID 2353717 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]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])([CH3:17])[CH3:16])[N:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=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>[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]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])([CH3:17])[CH3:16])[N:3]=[C:2]([C:35]2[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=2)[N:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59379947HCID 59379947, compound

Product 1

HCID 59380031HCID 59380031, compoundYield 100.1%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

trans-Dichlorobis (triphenylphosphine)palladium (II) (0.050 g, 0.07 mmol) was added to 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(2-pyridin-4-ylsulfonylpropan-2-yl)pyrimidine (0.560 g, 1.41 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.464 g, 2.12 mmol) and sodium carbonate (3.53 mL, 7.05 mmol) in 18% DMF in a mixture of DME:water:ethanol (7:3:2) (30 mL) at RT under nitrogen. The resulting solution was stirred at 80° C. for 5 hours. The reaction was allowed to cool and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice and the combined organics dried (MgSO4), filtered and evaporated to afford the desired material (0.640 g) which was used without further purification.

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate twice
  4. dry with materialthe combined organics dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ae25ee50859a4699ac3bc4ac603a531c
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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