Ethyl Acetate → HCID 67034301, compound

HRID 539014Notes

Reaction equation

HRID 539014 reaction equation
[NH2:1][C@@H:2]([CH:5]([CH3:7])[CH3:6])[CH2:3][OH:4].[Br:8][C:9]1[CH:10]=[N:11][N:12]2[CH:17]=[CH:16][C:15](Cl)=[N:14][C:13]=12.C(N(C(C)C)C(C)C)C.CCOC(C)=O>CN(C=O)C>[Br:8][C:9]1[CH:10]=[N:11][N:12]2[CH:17]=[CH:16][C:15]([NH:1][C@@H:2]([CH:5]([CH3:7])[CH3:6])[CH2:3][OH:4])=[N:14][C:13]=12

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 640993L-ValinolHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 67034301HCID 67034301, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-2-amino-3-methylbutan-1-ol (3.3 g, 32 mmol) in DMF was added 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (2.5 g, 11 mmol) and N-ethyl-N-isopropylpropan-2-amine (4.2 g, 32 mmol) and the reaction was heated to 100° C. for 4 hours. The reaction mixture was poured into EtOAc and washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to yield (S)-2-(3-bromopyrazolo[1,5-a]pyrimidin-5-ylamino)-3-methylbutan-1-ol (3.2 g, 99%). LCMS (APCI+) m/z 299, 301 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87f9a51b3bde4849a87d0898f2594334
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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