Cesium carbonate → HCID 57899399, compound

HRID 1024607Notes

Reaction equation

HRID 1024607 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[N:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:28]2[CH:33]=[CH:32][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl-].C(C1C=CC=C(C(C)C)C=1[N+:62]1[CH:66]=[CH:65][N:64]([C:67]2[C:72](C(C)C)=CC=CC=2C(C)C)C=1)(C)C.O1CCOCC1>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].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[N:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:28]2[CH:33]=[CH:32][C:31]([C:66]3[CH:65]=[N:64][CH:67]=[CH:72][N:62]=3)=[CH:30][CH:29]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 27349131,3-Bis(2,6-diisopropylphenyl)imidazolium chlorideHCID 57899389HCID 57899389, compound

Product 1

HCID 57899399HCID 57899399, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A reaction tube is charged with 6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one (32 mg, 0.053 mmol), 2-chloropyrizine (12.1 mg, 0.106 mmol), Cs2CO3 (34.5 mg, 0.106 mmol), Pd2(dba)3 (5.5 mg, 0.005 mmol), 1,3-bis-(2,6-diisopropyl-phenyl)-3H-imidazol-1-ium chloride (4.7 mg, 0.011 mmol) and anhydrous 1,4-dioxane (0.5 mL). The mixture is thoroughly degassed by alternately connecting the flask to vacuum and N2 for three times. The dark red reaction mixture is then heated at 90° C. for 16 h. The reaction mixture is then cooled down to room temperature and treated with H2O (10 mL). EtOAc is used for the extraction (3×3 mL). The combined extracts are concentrated under vacuum and purified by preparative LC/MS to provide the title compound. 1H NMR (CDCl3) δ (ppm) 9.03 (s, 1H), 8.93 (s, 1H), 8.66 (s, 1H), 8.55-8.60 (m, 2H), 8.07 (d, 1H), 7.99 (d, 2H), 7.83 (t, 1H), 7.52 (d, 2H), 7.37 (d, 2H), 7.16 (d, 2H), 3.14 (s, 1H). HPLC-MS calculated C27H17ClN6O (M+H+): 477.1, found: 477.1. HPLC-MS calculated C27H18ClN7O3S (M+H+): 556.1, found: 556.1

Workup

  1. customThe mixture is thoroughly degassed
  2. customThe dark red reaction mixture
  3. temperatureThe reaction mixture is then cooled down to room temperature
  4. extractionEtOAc is used for the extraction (3×3 mL)
  5. concentrationThe combined extracts are concentrated under vacuum
  6. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-0abc5bca8818451bba9fabd26974602b
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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