Isopropanol → HCID 86697425, compound

HRID 1478256Notes

Reaction equation

HRID 1478256 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.[NH2:12][CH2:13][CH2:14][N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(O)(C)C.C(N(CC)CC)C>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([NH:12][CH2:13][CH2:14][N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[N:7][C:6]=12

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 2756424N-Boc-N-methylethylenediamineHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 86697425HCID 86697425, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To 465 mg (2.00 mmol) of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine was added tert-butyl (2-aminoethyl)(methyl)carbamate (522 mg, 3.00 mmol), 4 mL of isopropanol, and triethylamine (0.56 mL, 4.00 mmol). The resulting mixture is heated at 140° C. for 0.5 hr in the microwave. It was diluted with EtOAc, and washed with water and brine. The organic layer was dried over MgSO4, concentrated and purified on the silica gel column eluting with 20-100% EtOAc/Hex to obtain 607 mg (82%) of the desired product.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. custompurified on the silica gel column
  5. washeluting with 20-100% EtOAc/Hex

Sources & evidence

ORD record
ord-0c5e9fc83b074618b9f251386672bab0
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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