Sodium Methoxide → HCID 67053374, compound

HRID 38369Notes

Reaction equation

HRID 38369 reaction equation
[CH3:1][O-].[Na+].Cl[CH2:5][CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[C:19]([NH2:25])=[N:20][C:21](N)=[N:22][CH:23]=2)[C:14]([CH:26]([CH3:28])[CH3:27])=[CH:13][C:12]=1[O:29][CH3:30])=[O:9]>CO>[NH2:25][C:19]1[C:18]([O:17][C:15]2[C:14]([CH:26]([CH3:28])[CH3:27])=[CH:13][C:12]([O:29][CH3:30])=[C:11]([N:10]3[CH2:5][CH2:6][CH2:7][C:8]3=[O:9])[CH:16]=2)=[CH:23][N:22]=[C:21]([CH3:1])[N:20]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 595985764-Chloro-N-[5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-butyramide

Product 1

HCID 67053374HCID 67053374, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5 ml 1.9 M NaOMe in MeOH was added 4-Chloro-N-[5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-butyramide (0.495 g, 1.3 mmol). After 6 h the solution was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with H2O, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give 1-[5-(4-amino-2-methyl-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-pyrrolidin-2-one (0.230 g, 47%) as white solid; [MH]+=358; mp (HCl salt)>300° C.

Workup

  1. concentrationAfter 6 h the solution was concentrated in vacuo
  2. washwashed with H2O
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b6d1e962eae45e2919964a115cbeaa0
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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