Methanol → HCID 69538213, compound

HRID 2216269Notes

Reaction equation

HRID 2216269 reaction equation
I[C:2]1[N:3]=[C:4]([NH2:23])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH3:22])[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH2:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH3:29].CO.CC#N>C(Cl)Cl.O>[CH:24](/[C:2]1[N:3]=[C:4]([NH2:23])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH3:22])[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])=[CH:25]\[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 887Methanol3×HCID 6342AcetonitrileHCID 115971-HexeneHCID 86592813HCID 86592813, compound

Product 1

HCID 69538213HCID 69538213, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

The reaction was performed with 2-iodo-8-ethylaminoadenosine (8, 740 mg, 1.70 mmol) and (E)-1-borocatechol)-1-hexene (5.09 mmol). The mixture was purfied by column chromatography (10–20% MeOH in CH2Cl2).Yield 23 mg (0.06 mmol, 5%), mp 128–130÷C; Rƒ 0.61 (20% MeOH in CH2Cl2); 1H NMR (MeOD-d4) δ 6.92–6.82 (m, 1H, ═CHCH2), 6.29 (d, 1H, J=14.04 Hz, ═CH), 6.02 (d, 1H, J =7.64 Hz<H-1′), 4.80–4.76 (m, 1H, H-2′), 4.29–4.27 (m, 1H, H-3′), 4.13–4.11 (m, 1H, H4′), 3.81 (q, 2H, J=10.89 Hz, H-5′), 3.42 (q, 2H, J=6.02 Hz, NHCH2), 2.24 (q, 2H, J=6.00 Hz, ═CHCH2), 1.53–1.33 (m, 4H, CH2CH2), 1.28 (t, 3H, J=7.72 Hz, NHCH2CH3), 0.94 (t, 3H, J=7.11 Hz, CH3); MS m/z 393 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=7.42 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=20.16 min.

Sources & evidence

ORD record
ord-62e11299d8bd4d5799f5d441b26a603e
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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