Diisopropylethylamine → N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2'-deoxyadenosine

HRID 871788

Reaction equation

HRID 871788 reaction equation
[C@@H:1]1([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13](O)[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.C(N(CC)C(C)C)(C)C.[I:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([NH2:37])[CH3:36])=[C:31]([N+:38]([O-:40])=[O:39])[CH:30]=1>CN(C=O)C>[I:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([NH:37][C:13]2[C:12]3[N:11]=[CH:10][N:9]([C:18]=3[N:17]=[CH:16][N:15]=2)[C@@H:1]2[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)[CH3:36])=[C:31]([N+:38]([O-:40])=[O:39])[CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 668309681-(4-Iodo-2-nitrophenyl)ethylamineHCID 178521064HCID 178521064, compound

Product 1

HCID 86620496N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2'-deoxyadenosine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 2′-deoxyinosine (150 mg, 0.6 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphonate (BOP, 379 mg, 0.86 mmol) in anhydrous DMF (1.5 mL), N,N-diisopropylethylamine (186 μL, 1.1 mmol) was added followed by the addition of a solution of 1-(4-iodo-2-nitrophenyl)ethylamine (460 mg, 1.57 mmol) in anhydrous DMF (0.5 mL). The mixture was stirred under nitrogen atmosphere for 48 hours. DMF was removed in vacuo, and the crude product was purified by silica gel column chromatography to yield N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2′-deoxyadenosine dA.20 (204 mg, 65%, 1:1 mixture of diastereomers) as a white foam.

Workup

  1. additionwas added
  2. customDMF was removed in vacuo
  3. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f8fb0adb2eb4fe3a5152f637490f8dc
Source dataset
uspto-grants-2015_03
Patent number
US08969535B2

Linked notes

Loading…