Dimethylformamide → 2-Amino-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-6-methoxypurine

HRID 467225Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[OH:11])=[C:4]([O:12][CH3:13])[N:3]=1.[CH3:14][C:15]1([CH3:23])[O:20][CH:19](C)[CH:18](I)[CH2:17][O:16]1.[C:24](=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:24][CH:18]2[CH2:17][O:16][C:15]([CH3:14])([CH3:23])[O:20][CH2:19]2)=[C:4]([O:12][CH3:13])[N:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 2-amino-9-hydroxy-6-methoxypurine (50mg, 0.276mmol), 2,2-dimethyl-5-iodo-methyl-1,3-dioxan (70.6mg, 0.276mmol), potassium carbonate (40.1mg, 0.290mmol) and dimethylformamide (1ml) was stirred at 20° C. for 3 hours. The suspension was diluted with chloroform (2ml), filtered and the filtrate evaporated to dryness. The residue was chromatographed on silica gel (eluted with chloroform-ethanol, 100:1) yielding the title compound (59.6mg, 70%). IR: υmax (KBr) 3396, 1640, 1581, 1480, 1390cm-1 ; 1H NMR: δH [(CD3)2SO] 1.32 (3H, s, CH3), 1.35 (3H, s, CH3), 2.00 (1H, m, CH), 3.77 (2H, dd, J=11.8, 6.1 Hz, 2×H(ax)), 3.96 (3H, s, OCH3), 3.99 (2H, dd, J=11.8, 4.1 Hz, 2×H(eq)), 4.36 (2H, d, J=6.8 Hz, CH2ON), 6.60 (2H, br.s, D2O exchangeable, NH2), 8.14 (1H, s, H-8). Found: C, 50.67; H, 6.31; N, 22.00%; m/e 309.1425. C13H19N5O4 + 0.2 EtOH requires: C, 50.53; H, 6.41; N, 21.99%; m/e 309.1434.

Workup

filtrationfiltered
customthe filtrate evaporated to dryness
customThe residue was chromatographed on silica gel (eluted with chloroform-ethanol, 100:1)

Sources & evidence

ORD record: ord-25a1fb81996646808c0017a35d7fc32e
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05159076

Reaction notes

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