Sodium Methoxide → HCID 11574672, compound

HRID 2056695Notes

Reaction equation

HRID 2056695 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15](S(C)(=O)=O)[N:14]=[C:13]([NH:21][C:22]3[CH:31]=[CH:30][C:25]4[O:26][CH2:27][CH2:28][O:29][C:24]=4[CH:23]=3)[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:32][O-:33].[Na+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([O:33][CH3:32])[N:14]=[C:13]([NH:21][C:22]3[CH:31]=[CH:30][C:25]4[O:26][CH2:27][CH2:28][O:29][C:24]=4[CH:23]=3)[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58612029HCID 58612029, compound

Product 1

HCID 11574672HCID 11574672, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 50-mL, round-bottomed flask containing a solution of 6-(4-tert-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(methylsulfonyl)pyrimidin-4-amine from step (c) above (0.20 g, 0.46 mmol) in MeOH (10 mL) was added NaOMe (76 mg, 1.4 mmol, Aldrich). The reaction mixture was refluxed for 2 h, and the solvent was removed in vacuo. Purification of the residue by silica gel column chromatography (4:1 hexane/EtOAc) provided the title product as a yellow solid. MS (ESI, pos. ion) m/z: 392 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customthe solvent was removed in vacuo
  3. customPurification of the residue by silica gel column chromatography (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-734889b9680c47bfa9fbd49673f4882c
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

Loading…