Cesium carbonate → HCID 67367052, compound

HRID 710577Notes

Reaction equation

HRID 710577 reaction equation
Cl[C:2]1[C:3]([C:8]2[CH:13]=[C:12]([S:14][CH3:15])[N:11]=[CH:10][N:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH2:16][C:17]1[C:22]([F:23])=[CH:21][N:20]=[C:19]([NH:24][S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])[C:18]=1[F:31].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:31][C:18]1[C:19]([NH:24][S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])=[N:20][CH:21]=[C:22]([F:23])[C:17]=1[NH:16][C:2]1[C:3]([C:8]2[CH:13]=[C:12]([S:14][CH3:15])[N:11]=[CH:10][N:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59486242HCID 59486242, compoundHCID 68266098HCID 68266098, compound

Product 1

HCID 67367052HCID 67367052, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 4-(3-chloropyrazin-2-yl)-6-(methylthio)pyrimidine (143 mg, 0.6 mmol), N-(4-amino-3,5-difluoropyridin-2-yl)propane-1-sulfonamide (100 mg, 0.4 mmol), Pd2(dba)3 (109 mg, 0.12 mmol), Xantphos (138 mg, 0.24 mmol), Cs2CO3 (389 mg, 1.19 mmol), 4 Å molecular sieves (500 mg) and dioxane (15 ml) was heated with stirring in a sealed vessel at 150° C. for 5 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated, then the residue was chromatographed on silica gel (10-30% ethyl acetate in hexanes eluant) to provide the title compound. MS m/z 454.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was chromatographed on silica gel (10-30% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-6ccdc7ca36d147d4ad8017ff1b9f8667
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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