Carbon Dioxide → HCID 21223938, compound

HRID 2073206Notes

Reaction equation

HRID 2073206 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[CH:15][C:16]([C:17]([NH2:19])=[O:18])=[C:12]3[NH:11][CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)=O.[H-].[Na+].[N:25]#[C:26]Br>O1CCCC1.O.CC(C)=O>[NH2:25][C:26]1[N:11]2[C:12]3[N:13]([C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)=[CH:9][CH2:10]2)[N:14]=[CH:15][C:16]=3[C:17](=[O:18])[N:19]=1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 136054883HCID 136054883, compound

Product 1

HCID 21223938HCID 21223938, compoundYield 6.9%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred suspension of 5.0 g of 7-(3-fluorophenyl)-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide (Example 6) in 250 ml of dry tetrahydrofuran, cooled to -78° C. (dry-ice, acetone) was added 1.70 g of sodium hydride (60% dispersion in mineral oil) in one portion. The reaction mixture was stirred at -78° C. for 30 minutes then 2.05 g of cyanogen bromide was added and the mixture was stirred for an additional 2 hours at -78° C., then slowly allowed to warm to room temperature over 16 hours. The reaction mixture was diluted with water and the solid was collected by filtration, washed with water, then ether to give 376 mg of the desired product as a white solid.

Workup

  1. stirringthe mixture was stirred for an additional 2 hours at -78° C.
  2. temperatureto warm to room temperature over 16 hours
  3. filtrationthe solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-658cca6b92904d8d87e53de435c427c5
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Reaction notes

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