Ammonia → 7-Deaza-7-iodo-2'-deoxyadenosine

HRID 1018032Notes

Reaction equation

HRID 1018032 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@@H:13]3[O:27][C@H:26]([CH2:28][O:29]C(C4C=CC(C)=CC=4)=O)[C@@H:15]([O:16]C(C4C=CC(C)=CC=4)=O)[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1.CO.C(Cl)Cl.CO>O1CCOCC1>[NH2:1][C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@@H:13]3[O:27][C@H:26]([CH2:28][OH:29])[C@@H:15]([OH:16])[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887Methanol2×HCID 15289163HCID 15289163, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 152891657-Deaza-7-iodo-2'-deoxyadenosine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

25% aqueous ammonia is added to 1.0 g (2.5 mmol) of 4-chloro-7-[2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythropentofuranosyl]-5-iodo-7H-pyrrolo[2,3-d]pyrimidine which is dissolved in 80 ml of dioxane (80 ml). The mixture is stirred in a steel cylinder at 110° C. for 48 h. After the solvent has been evaporated off, the concentrated residue is chromatographed on silica gel (20×5 cm column, solvent B). Colorless crystals from MeOH (0.75 g, 2.0 mmol, 45%). M.p. 194° C. TLC: Rf 0.4 (CH2Cl2/MeOH, 9:1). UV (MeOH) 283 nm (5 800). 1H-NMR (D6-DMSO): 2.16 (m, H-2′α), 2.46 (m, H-2′β, overlapped by DMSO), 3.54 (m, 2-H, H-5′), 3.81 (m, H-4′), 4.33 (m, H-3′), 5.00 (t, J=5.1 Hz, 5′-OH), 5.23 (d, J=5.1 Hz, 3′-OH), 6.49 (pt, J=6.7 Hz, H-1′), 6.65 (br, NH2), 7.65 (s, H-6), 8.10 (s, H-2). 13C-NMR (D6-DMSO) 157.3 (C-4), 152.0 (C-2), 149.8 (C-7a), 126.9 (C-6), 103.2 (C-4a), 87.5 (C-4′), 83.0 (C-1′), 71.0 (C-3′), 62.0 (C-5′), 51.9 (C-5), 39.8 (C-2′). Anal. calculated for C11H13IN4O3: C 35.13, H 3.48, N 14.90; found: C 35.33, H 3.69, N 15.01.

Workup

  1. customAfter the solvent has been evaporated off
  2. customthe concentrated residue is chromatographed on silica gel (20×5 cm column, solvent B)

Sources & evidence

ORD record
ord-fee54c79ec9f445e8d7303e5f4faa9b5
Source dataset
uspto-grants-2002_11
Patent number
US06479651B1

Reaction notes

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