Sodium hydride → HCID 19857888, compound

HRID 2073212Notes

Reaction equation

HRID 2073212 reaction equation
F[C:2](F)(F)[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)=O.CC(C)=O.[H-].[Na+].[C:32](N1C=CN=C1)(N1C=CN=C1)=[S:33]>O1CCCC1>[S:33]=[C:32]1[N:12]2[C:13]3[N:14]([C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([CH3:2])[CH:4]=4)=[CH:10][CH2:11]2)[N:15]=[CH:16][C:17]=3[C:18](=[O:19])[NH:20]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 27370934,5-Dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamideHCID 18522661Acetone cardice

Product 1

HCID 19857888HCID 19857888, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 1.00 g of 4,5-dihydro-7-(3-methyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (prepared as described in Example 4) in dry tetrahydrofuran cooled to -78° C. (dry ice-acetone) is added sodium hydride (60% dispersion in mineral oil). The reaction mixture is stirred at -78° C. for 30 minutes then 1,1'-thiocarbonyldiimidazole is added. The mixture is allowed to slowly warm to room temperature and is stirred for 36 hours. Then reaction mixture is quenched with water, neutralized with 5% aqueous hydrochloric acid and extracted with chloroform. Evaporation of the solvent in vacuo gives 4,5-dihydro-5-thioxo-8-(3-methylphenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringis stirred for 36 hours
  3. customThen reaction mixture
  4. customis quenched with water
  5. extractionextracted with chloroform
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-239324fadacd4b2b83e3b036cbb01578
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Reaction notes

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