Dimethylformamide → HCID 66825695, compound

HRID 1468626Notes

Reaction equation

HRID 1468626 reaction equation
[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[NH:11][CH:8]3[N:9]=2)=[C:5]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[N:4]=[CH:3]1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:37][CH:38]1[CH2:42][CH2:41][N:40]([C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)[CH2:39]1)(=O)=O>O>[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:37][CH:38]4[CH2:42][CH2:41][N:40]([C:43]5[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=5)[CH2:39]4)[CH:8]3[N:9]=2)=[C:5]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[N:4]=[CH:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66826441HCID 66826441, compoundHCID 86696641HCID 86696641, compound

Product 1

HCID 66825695HCID 66825695, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-amino-8-(2-furyl)-1-methyl-3H-[1,2,4]triazolo[5,1-f]purin-2-one (0.1 g, 0.368 mmol), DMF (3 ml), potassium carbonate (0.76 g, 0.553 mmol) and [1-(4-methoxyphenyl)pyrrolidin-3-yl]methyl methanesulfonate (0.115 g, 0.405 mmol) stirred at 60° C. for 48 hours. Reaction mixture was cooled to 0° C. Water was added and solid obtained was filtered off. The crude product was purified by HPLC/MS to obtain 5-amino-8-(2-furyl)-3-[[1-(4-methoxyphenyl)pyrrolidin-3-yl]methyl]-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one (0.012 g, 7%).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 0° C
  3. customsolid obtained
  4. filtrationwas filtered off
  5. customThe crude product was purified by HPLC/MS

Sources & evidence

ORD record
ord-49163389b4c842258d6fad03014e5fd3
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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