Ammonia → 2,6-Diamino-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)purine

HRID 1089270Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]1.[NH3:24]>CO>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]2[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]2)=[C:2]([NH2:24])[N:10]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-Chloro-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-2-formamidopurine (630 mg, 1.84 mmol), ammonia (10 ml) and methanol (15 ml) was heated at 110° C. for 7.5 hours in an autoclave and then allowed to cool over 16 hours. The mixture was evaporated to dryness and the residue chromatographed on silica (eluted with chloroform-ethanol, 20:1), affording the title compound (340 mg, 63%). 1R: υmax (KBr) 3409, 3321, 3158, 1669, 1640, 1589, 1488, 1457, 1409 cm-1. H NMR: δH [(CD3)2SO] 1.32(3H,s,CH3), 1.35(3H,s,CH3), 2.00(1H,m,CH3), 3.77(2H,dd, J=11.8, 6.1 Hz, 2×H(ax)), 3.98(2H,dd, J=11.8, 4.1 Hz, 2×H(eq)), 4.32(2H,d, J=7.1 Hz, CH2ON), 5.91(2H,br.s, D2O exchangeable, 6-NH2), 6.78(2H.br,s,D2O exchangeable, 2-NH2), 7.96(1H,s,H-8). Found: C, 48.34; H, 6.18; N, 28.21%; M+ 294.1437. C12H18N6O3 0.2H2O requires: C, 48.37; H, 6.24; N, 28.21%; M+ 294.1440.

Workup

temperatureto cool over 16 hours
customThe mixture was evaporated to dryness
customthe residue chromatographed on silica (eluted with chloroform-ethanol, 20:1)

Sources & evidence

ORD record: ord-2760a27ed7444b599f5b777af9e2fe99
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965270

Reaction notes

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