Methylamine → HCID 86592812, compound

HRID 2216258Notes

Reaction equation

C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[C:26]([I:29])[N:25]=[C:23]([NH2:24])[C:22]=2[N:21]=[C:20]1Br)(=O)C.[CH3:31][NH2:32]>>[I:29][C:26]1[N:25]=[C:23]([NH2:24])[C:22]2[N:21]=[C:20]([NH:32][CH3:31])[N:19]([C:28]=2[N:27]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

Reactant 2

HCID 6329Methylamine

HCID 12042145HCID 12042145, compound

Product 1

HCID 86592812HCID 86592812, compound

Procedure

The reaction was performed with 2′,3′,5′-tri-O-acetyl-2-iodo-8-bromoadenosine (6, 100 mg, 0.17 mmol) and methylamine (16 ml, 40% w/v in water). Yield 54.6 mg (0.13 mmol, 77%), mp 162–164÷C; 1H NMR (DMSO-d6) δ 7.02 (d, 1H, J=5.15 Hz, NH), 6.93 (s, 2H, NH2), 5.77 (d, 1H, J=7.56 Hz, H-1′), 5.66 (t, 1H, J=4.81 Hz, OH-2′), 5.31 (d, 1H, J=6.52 Hz, OH-5′), 5.18 (d, 1H, J=4.46 Hz, OH-3′), 4.56 (q, 1H, J=5.15 Hz, H-2′), 4.09–4.04 (m, 1H, H-3′), 3.98–3.91 (m, 1H, H-4′), 3.68–3.57 (m, 2H, H-5′), 2.86 (d, 3H, J=4.46 Hz, CH3); MS m/z 423 (M+H)+; Anal. (C11H15IN6O4) C, H, N.

Sources & evidence

ORD record: ord-8e9b31a802354847a4d5848faf459c2e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112574B2

Reaction notes

Loading…