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

HRID 524550Notes

Reaction equation

HRID 524550 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

4

Reactant 3

HCID 702EthanolHCID 59293633(4-Chloro-phenyl)-(2-hydrazino-9-methyl-9H-purin-6-yl)amineHCID 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.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe crude product was purified by flash chromatography (dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-1e3c51b7508942e8b0416dda08beb94d
Source dataset
uspto-grants-2016_05
Patent number
US09340544B2

Reaction notes

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