Ammonia → HCID 86748757, compound
Reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22](SC)=[N:23][C:24]=2Cl)(=O)C.Cl.[O:32]([CH2:39][CH2:40][O:41]ON)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([N:46](CC)CC)C.N>O1CCOCC1.C(OCC)(=O)C.CO>[O:32]([CH2:39][CH2:40][O:41][C:22]1[N:23]=[C:24]([NH2:46])[C:25]2[N:26]=[CH:27][N:19]([C:20]=2[N:21]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1Participants
Procedure
9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-2-methylthio-9H-purine (0.50 g, 1.1 mmol) (prepared by Method C, using the procedure described in PCT Publication No. WO 93/08206, O-[2-(phenoxy)ethoxy]hydroxylamine hydrochloride (0.41 g, 2.16 mmol) (see Example 9) and triethylamine (0.45 g, 4.4 mmol) were stirred at 100° C. in dioxan (20 ml) for 6 h, and at ca. 95° C. for 65 h. The product, after column chromatography, was deprotected using methanolic ammonia, to provide the title 2-methylthio-N-[2-(phenoxyethoxy]adenosine (0.09 g, 18%), (after column chromatography) as a colourless foam, tic Rf 0.26 [(SiO2, dichloromethane/methanol (9/1)], 1H NMR (DMSO-d6)γ 2.51 (3H, s,--SCH3), 3.52-3.60 (1H, m, H-5'a), 3.62-3.69 (1H, m, H-5'b), 3.94 (1H, q, H- 4'), 4.16 (1H, q, H-3'), 4.30 (4H, br d,--OCH2CH2O--), 4.61 (1H, q, H-2'), 5.04 (1H, t, 5'-OH), 5.23, 5.50 (2H, 9d, 9'- and 3'-OH), 5.90 (1H, d, H-1'), 6.92-7.01 (3H, m, Ar-H), 7.32 (2H, dd, Ar-H), 8.36 (1H, s, H-8), 11.20 (1H, s, N-H).
Sources & evidence
- ORD record
- ord-052cfce4d8cb4c2db0bd83e67a1d9ef6
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430027
Reaction notes
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