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

HRID 981532Notes

Reaction equation

HRID 981532 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].[Br-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C.C(O)C.C(N(CC)CC)C>[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

9

Reactant 5

HCID 6385Tert-ButylamineHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 253881Sodium BromideHCID 15729005HCID 15729005, compound

Product 1

HCID 1884028-tert-Butyl-6,7-dihydropyrrolo(3,2-e)-5-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrileYield 78.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8471TriethylamineSolvent

Procedure

(ii-2) A mixture of 7.0 g (0.026 mol) of Compound (VI) [R2 =CH3, R3 =CN], 6 ml of triethylamine, 15 ml of tert-butylamine, 0.1 g of sodium bromide micro-powder, 2.8 g of anhydrous sodium carbonate or potassium carbonate, 30 ml of anhydrous ethanol, and 100 ml of methyl ethyl ketone was reacted at 95° C. in an oil bath for 8 hours while stirring. The reaction solution was filtered while it was warm. The filtrate was purified using chromatography according to the same method as above to obtain Compound (I) [R1 =C(CH3)3, R2 =CH3, R3 =CN] at a yield of 78.5%.

Workup

  1. customwas reacted at 95° C. in an oil bath for 8 hours
  2. filtrationThe reaction solution was filtered while it
  3. temperaturewas warm
  4. customThe filtrate was purified

Sources & evidence

ORD record
ord-39e53411951e4e8288120f759e5925f5
Source dataset
uspto-grants-1991_02
Patent number
US04992442

Reaction notes

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