Dabco → HCID 178489346, compound
Reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C1N2CCN(CC2)C1.[H-].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[C:38]([CH2:39][OH:40])=[CH:37][C:36]2[C:31](=[C:32]([CH3:41])[CH:33]=[CH:34][CH:35]=2)[N:30]=1.N1C=C2C(N=CN2)=NC=1.C1N2CCN(CC2)C1>CS(C)=O>[N:10]1[C:2]([O:40][CH2:39][C:38]2[C:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][CH3:21])=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:41])=[C:3]2[C:7]([NH:6][CH:5]=[N:4]2)=[N:8][CH:9]=1Participants
Procedure
Prepared according to modified Procedure L. 6-Chloropurine (0.077 g, 0.5 mmol, 2 eq) and DABCO (0.112 g, 1 mmol, 4 eq) were stirred in DMSO (0.7 mL) at room temperature for 5 h. In a separate flask, sodium hydride (0.040 g, 1 mmol, 4 eq) was added portion-wise to a stirring solution of (2-(2-methoxyphenyl)-8-methyl-quinolin-3-yl)methanol (0.070 g, 0.25 mmol) in DMSO (0.5 mL), and after 30 minutes, the purine-DABCO salt was added to this mixture. The reaction stirred at room temperature 18 h. 3-((9H-purin-6-yloxy)methyl)-2-(2-methoxyphenyl)-8-methylquinoline [PI3Kδ IC50=38 nM] was isolated as a white solid after purification on a silica column. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.41 (1 H, s), 8.51 (1 H, s), 8.39 (1 H, s), 7.87 (1 H, d, J=7.8 Hz), 7.65 (1 H, d, J=7.0 Hz), 7.49-7.56 (1 H, m), 7.34-7.46 (2 H, m), 7.12 (1 H, d, J=8.2 Hz), 7.03 (1 H, t, J=7.2 Hz), 5.58 (2 H, s), 3.72 (3 H, s), 2.69 (3 H, s) Mass Spectrum (ESI) m/e=398.2 (M+1)
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-95e3f4fa3e51488680f46f066b167cee
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901135B2
Reaction notes
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