Sodium methanethiolate → 5'-Deoxy-5'-methylthio-8-methyladenosine

HRID 473584Notes

Reaction equation

HRID 473584 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][S-:22].[Na+]>CN(C=O)C>[CH3:21][S: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

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 251826935'-Chloro-5'-deoxy-8-methyladenosine

Product 1

HCID 252313105'-Deoxy-5'-methylthio-8-methyladenosine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3a (200 mg, 0.66 mmol) and sodium thiomethoxide (47 mg, 0.67 mmol) in 2 mL of anhydrous DMF was stirred for 2 days at room temperature and then concentrated to dryness. The crude product was purified by column chromatography using chloroform:methanol (7:1) as eluent. The desired fractions were collected, concentrated and dried in vacuo: yield 102 mg (49%); MS m/z 312 (M+H)+; 1HNMR (DMSO-d6) δ 8.09 (s, 1H, H-2), 7.12 (bs, 2H, 6-NH2), 5.77 (d, 1H, H-1′, J1′,2′=5.7 Hz), 5.38 (bd, 1H, OH-2′, J2′-2′OH=4.4 Hz), 5.31 (d, 1H, OH-3′, J3′-3′OH=4.2 Hz), 5.15 (bddd, 1H, H-2′, J1′,2′=5.7 Hz, J2′,3′=5.7 Hz, J2′-2′OH=4.4 Hz), 4.20 (ddd, 1H, H-3′, J2′,3′=5.7 Hz, J3′,4′=3.6 Hz, J3′-3′OH=4.2 Hz), 3.97-4.05 (m, 1H, H-4′), 2.74-2.92 (m, 2H, 5′-CH2), 2.54 (s, 3H, 8-CH3), 2.03 (s, 3H, S—CH3).

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude product was purified by column chromatography
  3. customThe desired fractions were collected
  4. concentrationconcentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ab584aeae34c4bf383c2eb56b4771a83
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Reaction notes

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