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

HRID 1809275Notes

Reaction equation

HRID 1809275 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-90ee272098dc4974a1e7f64a7d603e16
Source dataset
uspto-grants-2013_01
Patent number
US08362024B2

Reaction notes

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