Methanol → HCID 86592814, compound

HRID 2216260Notes

Reaction equation

HRID 2216260 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]([NH2:25])[CH2:23][CH3:24].CO>C(Cl)Cl>[I:21][C:15]1[N:16]=[C:17]([NH2:20])[C:18]2[N:19]=[C:2]([NH:25][CH2:22][CH2:23][CH3:24])[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

5

Reactant 3

HCID 887MethanolHCID 7852PropylamineHCID 86592810HCID 86592810, compound

Product 1

HCID 86592814HCID 86592814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction was performed with 2-iodo-8-bromoadenosine (5, 90 mg, 0.19 mmol) and propylamine (2.5 ml, 70% w/v in water). Yield 68.8 mg (0.15 mmol, 80%), mp 160–162÷C, Rƒ 0.20 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 6.99 (t, 1H, J=4.80 Hz, NH), 6.87 (s, 2H, NH2), 5.80 (d, 1H, J=8.24 Hz, H-1′), 5.67–5.63 (m, 1H, OH-2′), 5.30 (d, 1H, J=6.18 Hz, OH-5′), 5.18 (d, 1H, J=3.77 Hz, OH-3′), 4.56–4.51 (m, 1H, H-2′), 4.09–4.03 (m, 1H, H-3′), 3.96–3.94 (m, 1H, H-4′), 3.62–3.59 (m, 4H, H-5′, NHCH2), 1.57 (q, 2H, J=7.20 Hz, CH2CH3), 0.88 (t, 3H, J=7.50 Hz, CH3); MS m/z 451 (M+H)+; Anal. (C13H19IN6O4) C, H, N.

Sources & evidence

ORD record
ord-59d1e06e74a549f4b2c56c04b55423b2
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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