Water → HCID 67033394, compound

HRID 539027Notes

Reaction equation

HRID 539027 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]([CH:15]([CH3:17])[CH3:16])[CH2:13][NH2:14])=[N:7][C:6]=12.C(N(C(C)C)C(C)C)C.N1([C:32](N2C=CN=C2)=[O:33])C=CN=C1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:12]([CH:15]([CH3:17])[CH3:16])[CH2:13][NH:14][C:32]3=[O:33])=[N:7][C:6]=12

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 67035046(S)-N2-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-3-methylbutane-1,2-diamine

Product 1

HCID 67033394HCID 67033394, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)—N2-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-3-methylbutane-1,2-diamine (0.75 g, 2.52 mmol) in DMF was added N-ethyl-N-isopropylpropan-2-amine (1.38 ml, 7.55 mmol) and di(1H-imidazol-1-yl)methanone (0.816 g, 5.03 mmol) and the reaction stirred overnight at ambient temperature. The reaction was poured into water and extracted into EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude material was purified by chromatography, eluting with 2% MeOH/dichloromethane, to yield (S)-1-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-5-isopropylimidazolidin-2-one (0.48 g, 58%).

Workup

  1. extractionextracted into EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by chromatography
  6. washeluting with 2% MeOH/dichloromethane

Sources & evidence

ORD record
ord-ee2284e39713408787b51fe4f0dbedfe
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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