N-Methylethylenediamine → HCID 178510536, compound

HRID 2098066Notes

Reaction equation

HRID 2098066 reaction equation
[N:1]1[CH:2]=[N:3][N:4]2[C:9]=1[C:8]1[C:10]([C:13]#[N:14])=[CH:11][S:12][C:7]=1[N:6]=C2.CNCCN.[NH4+].[Cl-]>CO>[NH2:6][C:7]1[S:12][CH:11]=[C:10]([C:13]#[N:14])[C:8]=1[C:9]1[NH:1][CH:2]=[N:3][N:4]=1

Participants

5

Reactant 3

HCID 8014N-MethylethylenediamineHCID 25517Ammonium ChlorideHCID 68786598HCID 68786598, compound

Product 1

HCID 178510536HCID 178510536, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbonitrile (251 mg, 1.25 mmol) was dissolved in MeOH (6.2 mL), and N1-methylethane-1,2-diamine (0.22 mL, 2.5 mmol) was added. This was heated to 60° C. for 20 min, then immediately cooled in an ice bath. Saturated NH4Cl (30 mL) was added, then the aqueous mixture was extracted with 10% iPrOH/CHCl3 (3×). The organic layers were combined, dried (MgSO4), filtered and concentrated under reduced pressure to give the titled compound as a single peak on LC/MS: method [4], retention time=0.658 min; MS (ESI) 192.0 (MH+).

Workup

  1. temperatureimmediately cooled in an ice bath
  2. extractionthe aqueous mixture was extracted with 10% iPrOH/CHCl3 (3×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e69179fb17d456480f122decf5dd831
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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