Cesium carbonate → HCID 89996013, compound

HRID 1480843Notes

Reaction equation

HRID 1480843 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9](S(C)(=O)=O)[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH3:16])[N:3]=1.[CH2:17]([O:19][C:20]1[CH:25]=[C:24]([C:26]2[N:30]([CH3:31])[CH:29]=[N:28][N:27]=2)[CH:23]=[CH:22][C:21]=1[NH:32]C=O)[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O.O>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([NH:32][C:21]3[CH:22]=[CH:23][C:24]([C:26]4[N:30]([CH3:31])[CH:29]=[N:28][N:27]=4)=[CH:25][C:20]=3[O:19][CH2:17][CH3:18])[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH3:16])[N:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 89996199HCID 89996199, compoundHCID 89996206HCID 89996206, compound

Product 1

HCID 89996013HCID 89996013, compoundYield 27.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 8-chloro-6-methyl-2-(methylsulfonyl)pyrido[3,4-d]pyrimidine (Preparation 178, 31 mg, 0.120 mmol) in DMSO (5 mL) was added N-(2-ethoxy-4-(4-methyl-4H-1,2,4-triazol-3-yl)phenyl)formamide (Preparation 150, 35.5 mg, 0.144 mmol) and Cs2CO3 (78 mg, 0.241 mmol). The reaction mixture was heated to 120° C. for 18 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc (30 mL) and water (30 mL). The organic layer was washed with brine (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 50-100% EtOAc in cyclohexanes followed by elution through an SCX-2 column using MeOH—1M NH3 in MeOH to afford the title compound (12.9 mg, 27%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 50-100% EtOAc in cyclohexanes
  7. washfollowed by elution through an SCX-2 column

Sources & evidence

ORD record
ord-fa19acb79759443ea87689e9ee3be88f
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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