2-Aminopyrimidine → (1-Imidazo[1,2-a]pyrimidin-2-yl-ethyl)-carbamic acid benzyl ester

HRID 2036638Notes

Reaction equation

HRID 2036638 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH2:7].[CH2:8]([O:15][C:16](=[O:24])[NH:17][CH:18]([CH3:23])[C:19](=O)[CH2:20]Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCO>[CH2:8]([O:15][C:16](=[O:24])[NH:17][CH:18]([C:19]1[N:7]=[C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]2[CH:20]=1)[CH3:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 73196234Benzyl (4-bromo-3-oxobutan-2-yl)carbamate

Product 1

HCID 67432417(1-Imidazo[1,2-a]pyrimidin-2-yl-ethyl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of pyrimidin-2-ylamine (3 gm, 31.5 mmol) and (3-bromo-1-methyl-2-oxopropyl)-carbamic acid benzyl ester (9.4 gm, 31.54 mmol) in EtOH (20 mL) was heated to reflux overnight. After completion, the reaction mixture was cooled to rt and EtOH was removed in vacuo. The residue was dissolved in EtOAc and washed with satd. sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-5% MeOH in DCM to provide (1-imidazo[1,2-a]pyrimidin-2-yl-ethyl)-carbamic acid benzyl ester: LC-MS (ESI) m/z 297.1 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customEtOH was removed in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with satd
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ba2a394a80d048b4a7d673f538185b16
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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