Acetone → HCID 14814187, compound

HRID 1089254Notes

Reaction equation

C([O:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([NH2:15])=[N:9][C:10]=2[Cl:14])C=C.C[N+]1([O-])CC[O:20]CC1.[CH3:24][C:25]([CH3:27])=[O:26]>O.[Os](=O)(=O)(=O)=O>[NH2:15][C:8]1[N:7]=[C:6]2[C:11]([N:12]=[CH:13][N:5]2[O:4][CH2:24][CH:25]([OH:26])[CH2:27][OH:20])=[C:10]([Cl:14])[N:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 9-allyloxy-2-amino-6-chloropurine (374 mg, 1.66 mmol) and osmium tetroxide (catalytic) in acetone (10 ml) and water (10 ml) was treated with 4-methylmorpholine N-oxide (290 mg, 2.49 mmol) and stirred under nitrogen at 25° C. for 16 hours. The reaction was evaporated to dryness under reduced pressure and the residue chromatographed on silica gel (eluted with acetone) affording the title compound (325 mg, 76%), m.p. 173°-5° C. UV: λmax (MeOH) 224 (ε 26,400), 310 (ε 7,600) nm. IR: υmax (KBr) 3500, 3410, 3330, 3200, 3100, 1645, 1630, 1615, 1560, 1520, 1470 cm-1. 1H NMR: δH [(CD3)2SO] 3.42 (2H, m, CH2OH), 3.78 (1H, m, CHOH), 4.20 (1H, dd, J=10.7, 7.3 Hz, CH2ON), 4.41 ( 1H, dd, J=10.7, 3.2 Hz, CH2ON), 4.74 (1H, t, J=5.7 Hz, OH), 5.14 (1H, d, J=5.2 Hz), 7.13 (2H, br.s, NH2), 8.36 (1H, s, H-8). Found: C, 36.41; H. 3.91, N, 25.91%, M+ 259.0462. C8H10ClN5O3.0.3H2O requires C, 36.18; H, 4.04; N, 26.35%, M+ 259.0469.

Workup

customThe reaction was evaporated to dryness under reduced pressure
customthe residue chromatographed on silica gel (eluted with acetone)

Sources & evidence

ORD record: ord-6ea4f629bc02401294ff8e7cc6965144
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965270

Reaction notes

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