Methanol → HCID 86592815, compound

HRID 2216261Notes

Reaction equation

HRID 2216261 reaction equation
Br[C:2]1[N:3]([C:13]2[N:14]=[C:15]([I:21])[N:16]=[C:17]([NH2:20])[C:18]=2[N:19]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6].[CH2:22]([NH2:26])[CH2:23][CH2:24][CH3:25].O.CO>C(Cl)Cl>[I:21][C:15]1[N:16]=[C:17]([NH2:20])[C:18]2[N:19]=[C:2]([NH:26][CH2:22][CH2:23][CH2:24][CH3:25])[N:3]([C:13]=2[N:14]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8007ButylamineHCID 86592810HCID 86592810, compound

Product 1

HCID 86592815HCID 86592815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction was performed with 2-iodo-8-bromoadenosine (5, 1.15 g, 2.44 mmol) and n-butylamine (25 ml). Some drops of water were added to dissolve everything. Yield 0.92 g (1.98 mmol, 81%), mp 142–144÷C, Rƒ 0.23 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 6.94–6.86 (m, 3H, NH, NH2), 5.79 (d, 1H, J=7.56 Hz, H-1′), 5.67–5.62 (m, 1H, OH-2′), 5.30–5.16 (m, 2H, OH-3′,5′), 4.54–4.49 (m, 1H, H-2′), 4.07–4.04 (m, 1H, H-3′), 3.95–3.92 (m, 1H, H-4′), 3.64–3.57 (m, 2H, H-5′), 2.49–2.42 (m, 2H, NHCH2), 1.55–1.26 (m, 4H, CH2CH2CH3), 0.88 (t, 3H, J=7.21 Hz, CH3); MS m/z 464 (M+H)+; Anal. (C14H21IN6O4) C, H, N.

Workup

  1. dissolutionto dissolve everything

Sources & evidence

ORD record
ord-7347d71ab3434551b20bda7b0e993a3d
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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