Hydrochloric Acid → 7-(2-Chlorophenyl)-2-methyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one

HRID 2054382Notes

Reaction equation

HRID 2054382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([NH:13][C:14](=[NH:16])[CH3:15])[NH:11][N:12]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].Cl>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[N:13]=[C:14]([CH3:15])[NH:16][C:17](=[O:18])[N:11]2[N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 178465554HCID 178465554, compound

Product 1

HCID 1359745387-(2-Chlorophenyl)-2-methyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a pale yellow solution of N-[5-(2-chlorophenyl)-2H-pyrazol-3-yl]-acetamidine (I-1A-1b; 2.04 g, 8.69 mmol) in DMSO (17 mL) was added 1,1′-carbonyldiimidazole (1.53 g, 9.44 mmol), portionwise over 1 minute at room temperature. After stirring for one hour, the reaction was added to stirred 1 M aqueous HCl (17 ml) over 5 minutes. The colorless precipitate that formed was stirred for 2.5 hours and then collected on a course sintered funnel. The solids were washed with water (50 ml) and then dried on the frit under a stream of air using low vacuum to afford I-1A-1c as a colorless solid (2.29 g, quantitative): +APcI MS (M+1) 261.3.

Workup

  1. additionthe reaction was added
  2. customThe colorless precipitate that formed
  3. stirringwas stirred for 2.5 hours
  4. customcollected on a course sintered funnel
  5. washThe solids were washed with water (50 ml)
  6. customdried on the frit under a stream of air
  7. customto afford I-1A-1c as a colorless solid (2.29 g, quantitative)

Sources & evidence

ORD record
ord-62a376f97fd14400878db6ead1c3af92
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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