Ethanol → (4-Chloro-phenyl)-{9-methyl-2-[3-methyl-5-(tetrahydro-pyran-2-yloxymethyl)pyrazol-1-yl]-9H-purin-6-yl}-amine

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]#[C:9][C:10](=O)[CH3:11].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[N:29]=[C:28]([NH:30][NH2:31])[N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][N:25]3[CH3:32])=[CH:16][CH:15]=1.[CH2:33](O)C>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[N:29]=[C:28]([N:30]3[C:9]([CH2:8][O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)=[CH:10][C:11]([CH3:33])=[N:31]3)[N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][N:25]3[CH3:32])=[CH:16][CH:15]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 59293633(4-Chloro-phenyl)-(2-hydrazino-9-methyl-9H-purin-6-yl)amine

HCID 666163024-(Tetrahydro-pyran-2-yloxy)-but-3-yn-2-one

Product 1

HCID 59322258(4-Chloro-phenyl)-{9-methyl-2-[3-methyl-5-(tetrahydro-pyran-2-yloxymethyl)pyrazol-1-yl]-9H-purin-6-yl}-amineYield 12%

Procedure

4-(Tetrahydro-pyran-2-yloxy)-but-3-yn-2-on (824 mg, 4.5 mmol) and (4-chloro-phenyl)-(2-hydrazino-9-methyl-9H-purin-6-yl)-amine (1.5 g, 5.2 mmol) were dissolved in ethanol (30 mL) and heated at reflux for 24 hours. The reaction mixture was concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane/methanol/ammonia) to give (4-chloro-phenyl)-{9-methyl-2-[3-methyl-5-(tetrahydro-pyran-2-yloxymethyl)-pyrazol-1-yl]-9H-purin-6-yl}-amine (240 mg, 12%) as an yellow foam.