Diisopropylethylamine → HCID 86697441, compound

HRID 1478274Notes

Reaction equation

HRID 1478274 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8](Cl)=[N:7][C:6]=12.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C>C(O)(C)C.O>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:22]3[CH2:21][CH2:20][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:24][CH2:23]3)=[N:7][C:6]=12

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 86697441HCID 86697441, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (10 g, 43 mmol) taken up in isopropanol. T-butylpiperazine carboxylate (9.61 g, 51.6 mmol), diisopropylethylamine (22.4 mL, 129 mmol) added and stirred at 65° C. overnight. Reaction was cooled to room temperature, diluted with water and solid product filtered off. The solid was washed with water, dried to obtain 15.84 g crude product for further reaction, as is. LRMS (ESI) m/z 382/384 [(M+H)]+, calc'd for C15H20BrN5O2: 382.2.

Workup

  1. customReaction
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered off
  4. washThe solid was washed with water
  5. customdried

Sources & evidence

ORD record
ord-be8e51cab00b4b4d98c492e09f2c7f68
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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