Sodium Methoxide → HCID 59312304, compound

HRID 2077057Notes

Reaction equation

HRID 2077057 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15](Cl)=[N:16][C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22](Cl)[CH:21]=3)=[N:18][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][O-:29].[Na+]>CO>[CH2:19]([C:17]1[N:16]=[C:15]([O:29][CH3:28])[C:12]2[CH2:13][CH2:14][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10][C:11]=2[N:18]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59312360HCID 59312360, compound

Product 1

HCID 59312304HCID 59312304, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,7-dibenzyl-4-chloro-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine of Step B (86 mg, 0.23 mmol) was dissolved in methanol (10 ml) and sodium methoxide (25 mg, 0.47 mmol) was added. The reaction was refluxed under nitrogen for 16 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was separated, washed with brine (50 ml), dried over MgSO4, filtered and concentrated in vacuo to afford a colourless oil, 75.5 mg, 89%.

Workup

  1. temperatureThe reaction was refluxed under nitrogen for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
  4. customThe organic layer was separated
  5. washwashed with brine (50 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a colourless oil, 75.5 mg, 89%

Sources & evidence

ORD record
ord-528e709b92fa40db876b3c1cd229d716
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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