Imidazole → (1R,2S,3R,5R)-3-[6-Amino-9H-purin-9-yl]-5-[((2,3-dimethylbut-2-yl)dimethylsilyloxy)methyl]-1,2-cyclopentanediol

HRID 466240

Reaction equation

HRID 466240 reaction equation
[CH:1]1[N:6]=[C:5]2[N:7]([C@H:10]3[C@H:14]([OH:15])[C@H:13]([OH:16])[C@@H:12]([CH2:17][OH:18])[CH2:11]3)[CH:8]=[N:9][C:4]2=[C:3]([NH2:19])[N:2]=1.CN(C)C=O.N1C=CN=C1.[CH3:30][Si:31](Cl)([CH3:38])[C:32]([CH:35]([CH3:37])[CH3:36])([CH3:34])[CH3:33]>O>[NH2:19][C:3]1[N:2]=[CH:1][N:6]=[C:5]2[C:4]=1[N:9]=[CH:8][N:7]2[C@@H:10]1[CH2:11][C@H:12]([CH2:17][O:18][Si:31]([C:32]([CH3:34])([CH:35]([CH3:37])[CH3:36])[CH3:33])([CH3:38])[CH3:30])[C@@H:13]([OH:16])[C@H:14]1[OH:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 65269AristeromycinHCID 144239Dimethylthexylsilyl chloride2×

Product 1

HCID 15089637(1R,2S,3R,5R)-3-[6-Amino-9H-purin-9-yl]-5-[((2,3-dimethylbut-2-yl)dimethylsilyloxy)methyl]-1,2-cyclopentanediol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of aristeromycin (50 g) and dimethylformamide (250 ml) was stirred at room temperature and imidazole (50 g) and then dimethylthexylsilyl chloride (10 ml) were added. Three further 10 ml portions of dimethylthexylsilyl chloride were added after 20 min, 1 h and 1.75 h. After 4 h the resulting mixture was poured into rapidly stirred water (2.5 L). The suspension was filtered and the residue washed with water (2×250 ml). The air dried solid was added to di-isopropyl ether (500 ml) and stirred for 20 min. The suspension was filtered and the residue collected, stirred with diethyl ether (500 ml) and filtered to give the title compound (49 g); 1H nmr (DMSO-d6) δ8.13 (1H), 8.09 (1H), 7.18 (2H), 5.03-4.93 (1H), 4.76-4.60 (2H), 4.41-4.28 (1H), 3.88-3.78 (1H), 3.72-3.57 (2H), 2.28-1.70 (3H), 1.67-1.52 (1H), 0.95-0.75 (12H), 0.1 (6H).

Workup

  1. filtrationThe suspension was filtered
  2. washthe residue washed with water (2×250 ml)
  3. customThe air dried solid
  4. additionwas added to di-isopropyl ether (500 ml)
  5. stirringstirred for 20 min
  6. filtrationThe suspension was filtered
  7. customthe residue collected
  8. stirringstirred with diethyl ether (500 ml)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c0be78fd77224f0b9ea87f495985fd6e
Source dataset
uspto-grants-1992_10
Patent number
US05155112

Linked notes

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