Sodium Azide → (E)-6-azido-9-[2-(t-butyldiphenylsilyloxy)methyl-4-(diisopropoxyphosphoryl)but-3-enyl]purine

HRID 1708104Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH:12]([CH2:25][O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)/[CH:13]=[CH:14]/[P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:20])[CH3:19])=[O:16].[N-:44]=[N+:45]=[N-:46].[Na+]>CN(C)C=O>[N:44]([C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH:12]([CH2:25][O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)/[CH:13]=[CH:14]/[P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[N+:45]=[N-:46]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (E)-6-chloro-9-[2-(t-butyldiphenylsilyloxy)methyl-4-(diisopropoxyphosphoryl)but-3-enyl]purine (244 mg, 381 μmol) and sodium azide (25 mg, 381 μmol) in N,N-dimethylformamide (7 ml) was heated at 70° C. for 2.8 h. The solvent was removed and the residue purified by column chromatography on silica gel eluting with acetone-hexane (1:4, 1:1) to give (E)-6-azido-9-[2-(t-butyldiphenylsilyloxy)methyl-4-(diisopropoxyphosphoryl)but-3-enyl]purine as a gum (186 mg, 75%); λmax (EtOH) 282 (10,363)nm; υmax (film) 2980, 2935, 2155, 1640, 1375, 1250 and 1110 cm-1 ; δH (CDCl3) 1.00-1.40 (21H, m, CH3), 3.05 (1H, m, CH), 3.70 (2H, m, CH2O ), 4.30-4.80 (4H, m, CH2N and CH(CH3)), 5.58 (1H, m, PCH= CH) , 6.70 (1H, m, PCH=CH) , 7.30-7.70 (10H, m, C6H5) , 7.86 (0.35H, s, H-2/H-8), 8.05 (0.65H, s, H-2/H-8), 8.64 (0.35H, s, H-2/H-8), 9.44 (0.65H, s, H-2/H-8)*; FABMS (TDE/Na) 670 (MNa+), 648 (MH+).

Workup

customThe solvent was removed
customthe residue purified by column chromatography on silica gel eluting with acetone-hexane (1:4, 1:1)

Sources & evidence

ORD record: ord-22e3adf0e4494b949afbd5e61cc703de
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05356886

Reaction notes

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