5'-Chloro-5'-deoxy-8-(methylamino)adenosine → 5'-Deoxy-5',8-bis(methylamino)adenosine

HRID 473568Notes

Reaction equation

HRID 473568 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]2C)[C@H:6]([OH:20])[C@@H:5]1[OH:21].ClC[C@H]1O[C@@H:27]([N:29]2C3N=CN=C(N)C=3N=C2NC)[C@H](O)[C@@H]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[NH:29][CH3:27])[C@H:6]([OH:20])[C@@H:5]1[OH:21]

Participants

4

Reactant 2

HCID 252325375'-Chloro-5'-deoxy-8-(methylamino)adenosineHCID 252327175'-Deoxy-5'-methylamino-8-methyladenosine

Product 1

HCID 252327185'-Deoxy-5',8-bis(methylamino)adenosine

Reagents, catalysts & solvents 1

HCID 22028356Methylamine ethanolSolvent

Procedure

Compound 4c was prepared by the same procedure as described for the preparation of 4a using 3c (1.00 g, 3.17 mmol) and 33% methylamine/ethanol solution (30 mL). After column chromatography (elution with 7:1:0.4 chloroform:methanol:NH4OH), a yellow glassy solid was obtained: 505 mg (51%); MS m/z 310 (M+H)+; 1HNMR (DMSO-d6) δ 7.89 (bs and q, 2H, H-2 and 8CH3—NH), 6.44 (bs, 2H, 6-NH2), 5.84 (d, 1H, H-1′, J1′,2′=7.0 Hz), 5.22 (d, 1H, 2′-OH, J2′-2′OH=6.4 Hz), 5.12 (d, 1H, 3′-OH, J3′-3′OH=4.0 Hz), 4.66 (ddd, 1H, H-2′, J1′,2′=7.0 Hz, J2′,3′=5.4 Hz, J2′-2′OH=6.4 Hz), 4.14 (bm, 1H, H-3′), 3.94-4.0 (bm, 1H, H-4′), 2.90 (d, 3H, 8NH—CH3, J=4.4 Hz), 2.77-2.83 (m, 1H, 5′-CH2), 2.57-2.62 (m, 1H, 5′-CH2), 2.35 (s, 3H, 5′NH—CH3).

Workup

  1. washAfter column chromatography (elution with 7:1:0.4 chloroform:methanol:NH4OH)
  2. customa yellow glassy solid was obtained

Sources & evidence

ORD record
ord-60e6bc4213d14983b484bf77df5be868
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Reaction notes

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