Methanol → HCID 19789538, compound

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14]([O:26]C(=O)C)[CH2:15][S:16][C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[NH:19][CH:20]=[N:21]3)[CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+].CO>C(Cl)Cl>[OH2:26].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH:14]([OH:26])[CH2:15][S:16][C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[NH:19][CH:20]=[N:21]3)[CH2:11][CH2:12]1

Participants

Procedure

To 6-[1-[1-[2-pyridyl)piperazin-4-yl]-2-acetoxy-3-propanylthio]purine (0.30 g, 0.725 mmol) from Example 8in methanol (5 mL), was added anhydrous sodium bicarbonate (0.10 g, 0.725 mmol) at room temperature. After one week the methanol was removed in vacuo to give the crude product as a white solid. Silica gel flash chromatography using 10% methanol:methylene chloride gave the pure product as a white solid (0.260 g, 96.6%). mp 159°-161° C. DCI/MS (M+1) 372. 300 MHz1H NMR (DMSO-d6 and D2O) δ: 8.6 (s, 1H), 8.4 (s, 1H), 8.1 (m, 1H), 7.5 (m, 1H) 6.8 (d, 1H, J=8.59 Hz), 6.6 (m, 1H), 4.0 (m, 1H), 3.3 and 3.7 (q of q, 2H), 2.5 (m, 10H).