Cesium carbonate → HCID 59312356, compound

HRID 2077058Notes

Reaction equation

HRID 2077058 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10](Cl)[C:11]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13][C:12]=2[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](=O)([O-])[O-].[Cs+].[Cs+].CB1OB(C)OB(C)O1>O1CCOCC1>[CH2:1]([C:8]1[N:9]=[C:10]([CH3:27])[C:11]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13][C:12]=2[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 59312273HCID 59312273, compound

Product 1

HCID 59312356HCID 59312356, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,7-dibenzyl-4-chloro-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine (70 mg, 0.193 mmol) of Preparation 38, Step B, was dissolved in dioxane (5 ml) and Caesium carbonate (251 mg, 0.77 mmol), trimethylboroxine (0.054 ml, 0.385 mmol) and Catalyst 1 (10 mg) were added. The reaction was refluxed under nitrogen for 3 h. The reaction was filtered over arbocel and diluted with ethyl acetate, washed with water, dried over MgSO4 filtered and concentrated in vacuo to afford the title compound as a colourless oil in 99% yield, 66 mg.

Workup

  1. temperatureThe reaction was refluxed under nitrogen for 3 h
  2. filtrationThe reaction was filtered over arbocel
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b92495c0826445ca0d47629a592ede7
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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