Butyl iodide → 3-(4-Bromo-2-butyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660750Notes

Reaction equation

HRID 1660750 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[S:8][C:9]([C:13]2[C:14]([CH3:28])=[N:15][N:16]3[C:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:20][C:19]([CH3:27])=[N:18][C:17]=23)=[C:10]([Br:12])[N:11]=1.ICCCC.[Cl-].N>C1COCC1>[Br:12][C:10]1[N:11]=[C:7]([CH2:1][CH2:2][CH2:3][CH3:4])[S:8][C:9]=1[C:13]1[C:14]([CH3:28])=[N:15][N:16]2[C:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:20][C:19]([CH3:27])=[N:18][C:17]=12

Participants

6

Reactant 4

HCID 10962Butyl iodideHCID 20976574Ammonia chlorideHCID 674295502,4-Dibromo-5-(2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiazoleHCID 178418339Butyllithium

Product 1

HCID 674291383-(4-Bromo-2-butyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineYield 35.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, add n-butyl lithium (2.5 M in hexane, 0.2 mL, 0.5 mmol) to a solution of 3-(2,4-dibromo-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (230 mg, 0.5 mmol) in THF (3 mL) at −78° C. After 30 min, add 1-iodobutane (138 mg, 0.75 mmol) and continue stirring for 1 hour. Warm up to room temperature and stir for one hour. Quench the reaction by adding saturated ammonia chloride solution and extract with ethyl acetate. Dry the organic portion over sodium sulfate, filter, and concentrate to a residue. Purify the crude material by flash chromatography, eluting with hexanes/ethyl acetate (10/1.5) to give the title compound as orange foam (78 mg). ES/MS m/z (81Br) 437.4 (M+1)+.

Workup

  1. stirringstir for one hour
  2. customQuench
  3. customthe reaction
  4. extractionextract with ethyl acetate
  5. dry with materialDry the organic portion over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate to a residue
  8. customPurify the crude material by flash chromatography
  9. washeluting with hexanes/ethyl acetate (10/1.5)

Sources & evidence

ORD record
ord-8c52398663134741991bc5c084220cbd
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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