Adenine → 9-Ethyladenine

HRID 363712Notes

Reaction equation

HRID 363712 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.CN(C=O)C.[CH2:16]1COC[CH2:17]1>>[CH2:16]([N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])[CH3:17]

Participants

4

Reactant 3

HCID 190AdenineHCID 6228DimethylformamideHCID 8028Tetrahydrofuran

Product 1

HCID 79-EthyladenineYield 43%

Procedure

Coupling of 2b with adenine in THF in the presence of Ph3P and DEAD formed the desired N9 -substituted derivative 1a in only 5% yield. The low yield may be due to the insolubility of adenine in THF. After replacement of THF with DMF, compound 1a was produced in 43% yield without any detection of the N7 - derivative or the N9 -ethyladenine.

Workup

  1. customThe low yield may

Sources & evidence

ORD record
ord-b85d1adf9ae14e23bfa2a836e6a9cbab
Source dataset
uspto-grants-1999_02
Patent number
US05874577

Reaction notes

Loading…