Sodium Hydroxide → N9-phenethyl-8-(diethylphosphonomethyl-aminocarbonyl)adenine

HRID 1594620Notes

Reaction equation

[CH2:1]([N:9]1[C:17]([C:18]([O:20]C)=O)=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:22])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[NH2:25][CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C1COCC1.CO.O>[CH2:1]([N:9]1[C:17]([C:18]([NH:25][CH2:26][P:27]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:34])=[O:20])=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:22])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

N9-phenethyl-8-(methoxycarbonyl)adenine (1 mmol, prepared as in Step A of Example 5) was treated with sodium hydroxide (1.2 mmol) in THF:MeOH:H2O (3:2:1) at 25° C. for 1.5 h. The reaction mixture was evaporated to dryness, and the residue was dissolved in DMF, treated with diethyl aminomethylphosphonate (1.5 mmol), EDCl (1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride, 1.3 mmol), HOBt (1-hydroxy-benzotriazole hydrate, 1.5 mmol), and stirred at 25° C. for 24 h. Extraction and chromatography gave N9-phenethyl-8-(diethylphosphonomethyl-aminocarbonyl)adenine as a white solid. TLC: Rf=0.1, EtOAc.

Workup

customThe reaction mixture was evaporated to dryness
dissolutionthe residue was dissolved in DMF
extractionExtraction and chromatography

Sources & evidence

ORD record: ord-f84770cd07594bdea4daf2f6f5968d93
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284748B1

Reaction notes

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