Dimethylformamide → 8-tert-Butyl-6,7-dihydropyrrolo(3,2-e)-5-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrile

HRID 981533Notes

Reaction equation

HRID 981533 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9](C)[C:10]([C:11]#[N:12])=[C:6]2[N:5]=[C:4]([CH3:14])[C:3]=1[CH2:15][CH2:16]Cl.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(Cl)(Cl)Cl>[C:18]([N:22]1[C:2]2[N:7]3[N:8]=[CH:9][C:10]([C:11]#[N:12])=[C:6]3[N:5]=[C:4]([CH3:14])[C:3]=2[CH2:15][CH2:16]1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 15729005HCID 15729005, compound

Product 1

HCID 1884028-tert-Butyl-6,7-dihydropyrrolo(3,2-e)-5-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrileYield 87.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 88.9 g of Compound (VI) [R2 =H, R3 =CN], 33.0 g of tert-butylamine, 89 g of anhydrous potassium carbonate, and 700 ml of anhydrous dimethylformamide were stirred at room temperature overnight. To the reaction solution was added 500 ml of chloroform to remove insoluble substances by filtration. The filtrate was condensed under reduced pressure to dryness. The residue was dissolved in chloroform, washed with water, and dried over anhydrous sodium sulfate. The residue from which the solvent was evaporated was recrystallized in benzene to produce 73.6 g of 8-tert-butyl-3-cyano-6,7-dihydro-5-methyl-8H-pyrrolo [3,2-e]pyrazolo[1,5-a]pyrimidine [R1 =C(CH3)3, R2 =H, R3 =CN in formula (I)] having a melting point of 220°-224° C. at a yield of 82.8%.

Workup

  1. customto remove insoluble substances
  2. filtrationby filtration
  3. customcondensed under reduced pressure to dryness
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue from which the solvent was evaporated
  7. customwas recrystallized in benzene

Sources & evidence

ORD record
ord-8ad785d1a2834277bfbdf840f418ec4e
Source dataset
uspto-grants-1991_02
Patent number
US04992442

Reaction notes

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