Water → HCID 66825893, compound

HRID 1468627Notes

Reaction equation

HRID 1468627 reaction equation
[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:26][CH:25]=5)[CH2:20][CH2:19]4)[CH:8]3[N:9]=2)=[C:5]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[N:4]=[CH:3]1.[H-].[Na+].O.[CH3:43]N(C=O)C>>[O:36]1[CH:37]=[CH:38][CH:39]=[C:35]1[C:5]1[N:4]=[CH:3][N:2]([NH:1][CH3:43])[C:10]2[C:6]=1[N:7]1[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:28][CH:29]=4)[CH2:20][CH2:19]3)[CH:8]1[N:9]=2

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66824629HCID 66824629, compound

Product 1

HCID 66825893HCID 66825893, compound

Conditions

Temperature
21 °C

Procedure

A mixture of 5-amino-8-(2-furyl)-3-[2-[4-[4-(2-methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one (0.1 g, 0.18 mmol) obtained in example 1, NaH (0.043 g, 0.18 mmol) and methyl iodode (0.1 ml, 0.18 mmol)in DMF (2 ml) were stirred at 21° C. for 3 hours. To the reaction mixture water (10 ml) was added and solid obtained was filtered. The crude product was purified by column chromatography to obtain 8-(2-furyl)-3-[2-[4-[4-(2-methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-1-methyl-5-(methylamino)-[1,2,4]triazolo[5,1-f]purin-2-one. (5 mg, 5%) as an off white solid.

Workup

  1. customsolid obtained
  2. filtrationwas filtered
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0e090a61e4404095a9c36e99b8ed8c4c
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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