5'-Chloro-5'-deoxy-8-phenyladenosine → 5'-Deoxy-5'-methylamino-8-phenyladenosine

HRID 473569Notes

Reaction equation

HRID 473569 reaction equation
[CH3:1][NH:2][CH2:3][C@H:4]1[O:8][C@@H:7]([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[C:10]2[CH3:19])[C@H:6]([OH:20])[C@@H:5]1[OH:21].Cl[CH2:23][C@H:24]1O[C@@H:27](N2C3N=CN=C(N)C=3N=C2C2C=CC=CC=2)[C@H:26](O)[C@@H:25]1O>CN.C(O)C>[CH3:1][NH:2][CH2:3][C@H:4]1[O:8][C@@H:7]([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[C:10]2[C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:6]([OH:20])[C@@H:5]1[OH:21]

Participants

4

Reactant 2

HCID 251826965'-Chloro-5'-deoxy-8-phenyladenosineHCID 252327175'-Deoxy-5'-methylamino-8-methyladenosine

Product 1

HCID 252320025'-Deoxy-5'-methylamino-8-phenyladenosine

Reagents, catalysts & solvents 1

HCID 22028356Methylamine ethanolSolvent

Procedure

Compound 4d was prepared by the same procedure as described for the preparation of 4a using 3d (2.00 g, 5.52 mmol) and 33% methylamine/ethanol solution (40 mL). After column chromatography (elution with 4:1:0.2 chloroform:methanol:NH4OH), a yellow glassy solid was obtained: 963 mg (49%); MS m/z 357 (M+H)+; 1HNMR (DMSO-d6) δ 8.19 (s, 1H, H-2), 7.72-7.76 (m, 2H, 8-phenyl o-H's), 7.58-7.61 (m, 3H, 8-phenyl m- and p-H's), 7.40 (bs, 2H, 6-NH2), 5.70 (d, 1H, H-1′, J1′,2′=6.4 Hz), 5.38 (d, 1H, 2′-OH, J2′-2′OH=6.2 Hz), 5.29 (ddd, 1H, H-2′, J1′,2′=6.4 Hz, J2′,3′=5.1 Hz, J2′-2′OH=6.2 Hz), 5.14 (bs, 1H, 3′-OH), 4.19 (bs, 1H, H-3′), 3.95-4.0 (m, 1H, H-4′), 2.82 (d, 2H, 5′-CH2, J=5.2 Hz), 2.34 (s, 3H, 5′NH—CH3).

Workup

  1. washAfter column chromatography (elution with 4:1:0.2 chloroform:methanol:NH4OH)
  2. customa yellow glassy solid was obtained

Sources & evidence

ORD record
ord-d9c36a3e6bcc4b70b0f9593ea3fc3872
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Reaction notes

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