Dimethylformamide → HCID 2586924, compound

HRID 1752778Notes

Reaction equation

HRID 1752778 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([SH:12])[N:11]=[C:4]2[N:3]=1.Br[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][S:12][C:10]2[N:11]=[C:4]3[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]3[N:9]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 178426287HCID 178426287, compound

Product 1

HCID 2586924HCID 2586924, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5,7-dimethyl-[1,2,4]-triazolo[1,5-a]pyrimidine-2-thiol (1.0 g, 5.6 mmol), 1-(2-bromoethoxy)-4-chlorobenzene (1.19 g, 5.1 mmol), potassium carbonate (1.75 g, 12.6 mmol), and anhydrous N,N-dimethylformamide (6 mL) was added to a 20 mL scintillation vial with a magnetic stirring bar. The vial was capped loosely and the mixture allowed to stir at room temperature for 30 minutes. Progress of the reaction was monitored by analytical HPLC with UV detection (Rt=8.28 min). The mixture contained solids starting at 30 minutes and was stopped stirring at 1 hour. The mixture was transferred into an Erlenmeyer flask with a total of 70 mL of water, and allowed to stir for 10 min. The resulting solid was isolated by filtration, rinsed with 100 mL of water, and allowed to dry under reduced pressure. The off-white powder was >90% pure by analytical HPLC with UV detection at 215 nm. The solid was dissolved in 25 mL of ethanol with gentle warming, diluted with 5 mL of water and allowed to cool. The fine white needles that formed were isolated by filtration, washed with 20 mL of cold ethanol, and dried to afford the title compound (1.43 g, 85% yield). EM (calc.): 334.1; MS (ESI) m/e: 335.1 (M+H)+. 1H NMR (DMSO-d6, 400 MHz) δ ppm: 7.31 (d, 2H), 7.12 (s, 1H), 7.03 (d, 2H), 4.33 (t, 2H), 3.60 (t, 2H), 2.68 (s, 3H), 2.55 (s, 3H).

Workup

  1. additionwas added to a 20 mL scintillation vial with a magnetic stirring bar
  2. customThe vial was capped loosely
  3. waitstarting at 30 minutes
  4. stirringwas stopped stirring at 1 hour
  5. stirringto stir for 10 min
  6. customThe resulting solid was isolated by filtration
  7. washrinsed with 100 mL of water
  8. customto dry under reduced pressure
  9. dissolutionThe solid was dissolved in 25 mL of ethanol with gentle warming
  10. additiondiluted with 5 mL of water
  11. temperatureto cool
  12. customThe fine white needles that formed
  13. customwere isolated by filtration
  14. washwashed with 20 mL of cold ethanol
  15. customdried

Sources & evidence

ORD record
ord-2ed4ee32b9e94e73a1d8ba86d25bb6de
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

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