Methylamine → 2',3'-Dideoxy-N^6-methyl-4'-thioadenosine

HRID 2260894Notes

Reaction equation

HRID 2260894 reaction equation
[CH:1]1([N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3Cl)[S:5][C@H:4]([CH2:6][OH:7])[CH2:3][CH2:2]1.[CH3:18][NH2:19]>O>[CH3:18][NH:19][C:13]1[C:14]2[N:15]=[CH:16][N:8]([C:9]=2[N:10]=[CH:11][N:12]=1)[C@@H:1]1[S:5][C@H:4]([CH2:6][OH:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 151261019-(4-Thio-2,3-dideoxy-D-ribofuranosyl)-6-chloropurine

Product 1

HCID 4537572',3'-Dideoxy-N^6-methyl-4'-thioadenosineYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The anomeric mixture of 20 (0.132 g, 0.49 mmol) in a steel bomb was stirred with 20 mL 40% methylamine in water at 80° C. overnight. After solvent removal in vacuo, the residue was purified by preparative TLC with 9:1 chloroform/methanol to give 100 mg (77%) of the anomeric mixture. The anomers were partially separated by a Dowex 1×4 (--OH) column with 10% aqueous methanol to give 37 mg of impure β anomer which was recrystallized from hexane-ethyl acetate to afford 22.5 mg of pure β anomer by HPLC; mp. 131°-134° C.; FAB MS 266 (M +H)+ ; 1H NMR (DMSO-d6) δ 8.4 (s, 1, H-2), 8.2 (s, 1, H-8), 7.7 (brs, 1, NH), 6.2 (m, 1, i'-H), 5.15 (m, 1, 5'-OH), 3.75 (m, 1, 5'-H), 3.6 (m, 2, 4'-H, 5'-H), 2.95 (s, 3, CH3), 2.4 (m, 2, 4'-H's), 2.15 (m, 1, 3'-H), 2.0 (m, 1, 3'-H).

Workup

  1. customAfter solvent removal in vacuo
  2. customthe residue was purified by preparative TLC with 9:1 chloroform/methanol

Sources & evidence

ORD record
ord-34aae825ae174d598ab70c1e685dc81d
Source dataset
uspto-grants-1995_12
Patent number
US05478928

Reaction notes

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