Tert-Butylamine → HCID 15729016, compound

HRID 981534Notes

Reaction equation

HRID 981534 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:13])[C:10](C#N)=[C:6]2[N:5]=[C:4]([CH3:14])[C:3]=1[CH2:15][CH2:16]Cl.C(=O)([O-])[O-].[K+].[K+].[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25]>CN(C)C=O>[C:24]([N:28]1[C:2]2[N:7]3[N:8]=[C:9]([C:13]4[CH:16]=[CH:15][CH:3]=[CH:4][CH:14]=4)[CH:10]=[C:6]3[N:5]=[C:4]([CH3:14])[C:3]=2[CH2:15][CH2:16]1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

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

Product 1

HCID 15729016HCID 15729016, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 16.11 g of Compound (VI) [R2 =H, R3 =H], 38 g of anhydrous potassium carbonate, 5.85 g of tert-butylamine, and 140 ml of dimethylformamide was heated at 50°-60° C. in a water bath for 2 days while stirring. The reaction mixture was cooled and filtered. The filtrate was evaporated under reduced pressure. The residue was dissolved in 150 ml of chloroform. The chloroform layer was washed with water and evaporated under reduced pressure to obtain 15.72 g of an oily substance. The oily substance was purified using silica gel chromatography, followed by recrystallizing in a mixed solvent of benzene-isopropylether-hexane to produce 8-tert-butyl-6,7-dihydro-5-methyl-8H-pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidine [R1 =C(CH3)3, R2 =H, R3 =H in formula (I)] (Compound 11 of this invention) as light yellow plate crystals having a melting point of 147°-149° C. at a yield of 70.1%.

Workup

  1. temperaturewas heated at 50°-60° C. in a water bath for 2 days
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 150 ml of chloroform
  6. washThe chloroform layer was washed with water
  7. customevaporated under reduced pressure
  8. customto obtain 15.72 g of an oily substance
  9. customThe oily substance was purified
  10. customby recrystallizing in a mixed solvent of benzene-isopropylether-hexane

Sources & evidence

ORD record
ord-807390da466b415ba5974be0d4302e91
Source dataset
uspto-grants-1991_02
Patent number
US04992442

Reaction notes

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