1,1'-Carbonyldiimidazole → (R)-3-(2-Cyclopropyl-8-oxo-7,8-dihydro-purin-9-yl)-3-phenyl-propionic acid ethyl ester

HRID 2175203Notes

Reaction equation

HRID 2175203 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][N:17]=[C:16]([CH:21]2[CH2:23][CH2:22]2)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C1N=CN([C:30](N2C=NC=C2)=[O:31])C=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([N:13]1[C:30](=[O:31])[NH:20][C:19]2[C:14]1=[N:15][C:16]([CH:21]1[CH2:22][CH2:23]1)=[N:17][CH:18]=2)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 58497455(R)-3-(5-Amino-2-cyclopropyl-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497396(R)-3-(2-Cyclopropyl-8-oxo-7,8-dihydro-purin-9-yl)-3-phenyl-propionic acid ethyl esterYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-3-(5-Amino-2-cyclopropyl-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester (880 mg, 2.7 mmol) was dissolved in THF (10 ml). To the solution CDI was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with Ethyl acetate (100 ml) washed with water, dried over MgSO4, filtered and evaporated to dryness. The black residue obtained was purified by chromatography, eluded with 3% methanol in dichloromethane to give oil (427 mg, 45%).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe black residue obtained
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-bb8c2dd75210417980e1e74af084bf40
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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