Methylamine ethanol → 5'-Deoxy-5'-methylamino-8-methyladenosine

HRID 473566Notes

Reaction equation

HRID 473566 reaction equation
Cl[CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[C:9]2[CH3:18])[C@H:5]([OH:19])[C@@H:4]1[OH:20].[CH3:21][NH2:22].C(O)C>>[CH3:21][NH:22][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[C:9]2[CH3:18])[C@H:5]([OH:19])[C@@H:4]1[OH:20]

Participants

3

Reactant 2

HCID 22028356Methylamine ethanolHCID 251826935'-Chloro-5'-deoxy-8-methyladenosine

Product 1

HCID 252327175'-Deoxy-5'-methylamino-8-methyladenosine

Conditions

Temperature
90 °C

Procedure

A mixture of 3a (660 mg, 2.20 mmol) in 33% methylamine/ethanol solution (30 mL) in a steel bomb was heated for 2 days at 90° C. The reaction mixture was concentrated to dryness and purified by column chromatography (elution with 4:1:0.3 chloroform:methanol:NH4OH). The desired fractions were combined, concentrated and dried in vacuo: yield 294 mg (45%); MS m/z 295 (M+H)+; 1HNMR (DMSO-d6) δ 8.08 (bs, 1H, H-2), 7.14 (bs, 2H, 6-NH2), 5.72 (d, 1H, H-1′, J1′,2′=6.5 Hz), 5.30 (d, 1H, 2′-OH, J2′-2′OH=6.3 Hz), 5.17 (bd, 1H, 3′-OH, J3′-3′OH=3.5 Hz), 5.01 (ddd, 1H, H-2′, J1′,2′=6.5 Hz, J2′,3′=5.5 Hz, J2′-2′OH=6.3 Hz), 4.16 (bs, 1H, H-3′), 3.96-4.0 (m, 1H, H-4′), 2.64-2.77 (bm, 2H, 5′-CH2), 2.53 (s, 3H, 8-CH3), 2.29 (s, 3H, 5′NH—CH3).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by column chromatography (elution with 4:1:0.3 chloroform:methanol:NH4OH)
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ba06a80a57754755bc2e1f96e2581fda
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Reaction notes

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