Toluene → Isopropyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

HRID 1844356Notes

Reaction equation

HRID 1844356 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][C:6]=12.[CH:17]([O:20][C:21](Cl)=[O:22])([CH3:19])[CH3:18].C1(C)C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:21]([O:20][CH:17]([CH3:19])[CH3:18])=[O:22])[CH2:13][CH2:12]3)=[N:7][C:6]=12

Participants

6

Reactant 4

HCID 1140TolueneHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 866974343-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 86697433Isopropyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine (2.5 g, 8.87 mmol) taken up in DCM. Isopropylchloroformate 1M in toluene (13.3 mL, 13.3 mmol), and triethylamine (2.47 mL, 17.7 mmol) added and stirred at room temperature 30 minutes. Reaction washed with water, DCM layer dried over magnesium sulfate filtered reduced in vacuo. Run on an Isco silica column with DCM:MeOH 0-5%. Product fractions were combined and reduced in vacuo to obtain 2.86 g crude product for further reaction as is. LRMS (ESI) m/z 368/370 [(M+H)]+, calc'd for C14H18BrN5O: 368.24.

Workup

  1. customReaction
  2. washwashed with water, DCM layer
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8f55bd42f8f84712afc3e5688d631c64
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

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