6-(Phenylmethoxy)-9H-purin-2-amine → HCID 76623249, compound

HRID 1797418Notes

Reaction equation

HRID 1797418 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[H-].[Li+].[CH3:21][Si:22]([CH3:46])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH:23]1[CH2:28][CH:27]2[C:25]([CH2:29][OH:30])([O:26]2)[CH:24]1[CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:27]2[C:25]([OH:26])([CH2:29][OH:30])[CH:24]([CH2:31][O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:23]([Si:22]([CH3:46])([CH3:21])[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:28]2)=[C:4]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:3]=1

Participants

6

Reactant 3

HCID 45786-(Phenylmethoxy)-9H-purin-2-amineHCID 62714Lithium hydrideHCID 86594449HCID 86594449, compound

Product 1

HCID 76623249HCID 76623249, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a 1-L 3-necked round bottomed flask equipped with a mechanical stirrer and a thermometer, was charged 2-amino-6-benzyloxypurine (24 g, 0.1 moles), lithium hydride (0.48 g, 0.06 moles) and DMF (40 mL). The mixture was heated at 60° C. for about 1 hour under an atmosphere of argon. 77 (60 g, 0.1 moles) in 20 mL DMF was added. The reaction temperature was heated at 105° C. for 5 hours, cooled to room temperature and diluted with EtOAc (600 mL). The organic layer was washed with brine (300 mL), 1 M citric acid (150 mL), and NaHCO3 solution (100 mL). The organic layer was concentrated in vacuo to furnish crude title product (60 g) as an oil. It was crystallized from EtOAc and hexane to give 23 g of the title compound as a crystalline solid.

Workup

  1. customTo a 1-L 3-necked round bottomed flask equipped with a mechanical stirrer
  2. temperatureThe reaction temperature was heated at 105° C. for 5 hours
  3. temperaturecooled to room temperature
  4. washThe organic layer was washed with brine (300 mL), 1 M citric acid (150 mL), and NaHCO3 solution (100 mL)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customto furnish crude title product (60 g) as an oil
  7. customIt was crystallized from EtOAc and hexane

Sources & evidence

ORD record
ord-50fe282823d8406893c45c727ada13e3
Source dataset
uspto-grants-2006_04
Patent number
US07034152B2

Reaction notes

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