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Sodium Bicarbonate → (rac)-7-(4-Cyanophenyl)-5-methyl-2-thiophen-2-yl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 1046824
Notes
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Reaction equation

HRID 1046824 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([NH2:11])[NH:8][N:7]=1.[C:12]([C:14]([C:24](=O)[CH3:25])=[CH:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)#[N:13].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH:15]2[N:8]3[N:7]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[N:10]=[C:9]3[NH:11][C:24]([CH3:25])=[C:14]2[C:12]#[N:13])=[CH:17][CH:18]=1)#[N:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 666280804-(2-Cyano-3-oxobut-1-en-1-yl)benzonitrileHCID 178508309HCID 178508309, compound

Product 1

HCID 136355665(rac)-7-(4-Cyanophenyl)-5-methyl-2-thiophen-2-yl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
55 °C

Procedure

Under an atmosphere of argon, 3-(2-thienyl)-1H-1,2,4-triazole-5-amine (318 mg, 1.9 mmol) and 4-(2-cyano-3-oxobut-1-en-1-yl)benzonitrile (300 mg, 1.5 mmol, 0.8 eq.) were dissolved in DMF (3 ml), and solid sodium bicarbonate (803 mg, 9.6 mmol, 5 eq.) was added. The mixture was stirred at 55° C. for 12 h. The mixture was then filtered, and the DMF from the filtrate was distilled off under reduced pressure. The residue was purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). The product was obtained as a solid (73.7 mg, 91% pure, 12% of theory).

Workup

  1. filtrationThe mixture was then filtered
  2. distillationthe DMF from the filtrate was distilled off under reduced pressure
  3. customThe residue was purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customThe product was obtained as a solid (73.7 mg, 91% pure, 12% of theory)

Sources & evidence

ORD record
ord-9f1258e5fd6240d4896b13513659a24f
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569314B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes