2,2,6,6-Tetramethyl-3,5-heptanedione → HCID 21192075, compound

HRID 1067146Notes

Reaction equation

HRID 1067146 reaction equation
[CH3:1][C:2]([CH3:13])([C:4](=O)[CH2:5][C:6](=O)[C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:3].Cl.[N+:15]([C:18]1[CH:22]=[N:21][NH:20][C:19]=1[NH2:23])([O-:17])=[O:16]>C(O)(=O)C>[C:2]([C:4]1[CH:5]=[C:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:20]2[N:21]=[CH:22][C:18]([N+:15]([O-:17])=[O:16])=[C:19]2[N:23]=1)([CH3:13])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 22676973HCID 22676973, compound

Product 1

HCID 21192075HCID 21192075, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

36.85 g of 2,2,6,6-tetramethyl-3,5-heptanedione, 200 cc of acetic acid and 32.91 g of 4-nitro-2H-pyrazol-3-ylamine hydrochloride (prepared in accordance with H. Dorn and H. Dilcher, Liebigs Ann. Chem., 707,141, 1967) were introduced into a 500 ml three-necked flask fitted with a condenser, a thermometer and a magnetic bar. The mixture was refluxed for 8.5 hours. The solution was poured, hot, onto ice. The yellow solid which precipitated was filtered off. It was recrystallized from an acetic acid/water mixture. Drying under vacuum and over phosphoric anhydride yielded 25.4 g of 5,7-di-tert-butyl-3-nitropyrazolo[1,5-a]pyrimidine (yield=46%).

Workup

  1. customfitted with a condenser
  2. temperatureThe mixture was refluxed for 8.5 hours
  3. additionThe solution was poured
  4. customThe yellow solid which precipitated
  5. filtrationwas filtered off
  6. customIt was recrystallized from an acetic acid/water mixture
  7. dry with materialDrying under vacuum and over phosphoric anhydride

Sources & evidence

ORD record
ord-9858d519fb984fa48df486c1cbea05a0
Source dataset
uspto-grants-2001_06
Patent number
US06248137B1

Reaction notes

Loading…