Ammonium Chloride → 3-(4-Chloro-2-methoxymethyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660752Notes

Reaction equation

HRID 1660752 reaction equation
C([Li])CCC.[CH2:6]([CH:8]([C:11]1[N:16]2[N:17]=[C:18]([CH3:28])[C:19]([C:20]3[S:24][C:23]([CH2:25][O:26][CH3:27])=[N:22][CH:21]=3)=[C:15]2[N:14]=[C:13]([CH3:29])[CH:12]=1)[CH2:9][CH3:10])[CH3:7].[Cl:30]N1C(=O)CCC1=O.[Cl-].[NH4+]>C1COCC1>[Cl:30][C:21]1[N:22]=[C:23]([CH2:25][O:26][CH3:27])[S:24][C:20]=1[C:19]1[C:18]([CH3:28])=[N:17][N:16]2[C:11]([CH:8]([CH2:9][CH3:10])[CH2:6][CH3:7])=[CH:12][C:13]([CH3:29])=[N:14][C:15]=12

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31398ChlorosuccinimideHCID 674280047-(1-Ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 674285973-(4-Chloro-2-methoxymethyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineYield 4.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add n-butyl lithium (2.5 M in hexanes, 174 mL, 0.43 mmol) to a stirred solution of 7-(1-ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (150 mg, 0.43 mmol) in THF (3 mL) at −78° C. Stir for 30 min and add N-chlorosuccinimide (87 mg, 0.653 mmol). Stir 30 min and then warm the reaction slowly to room temperature allowing the reaction to continue overnight. Quench the reaction by adding saturated ammonium chloride solution, extract with ethyl acetate, dry over sodium sulfate, filter, and concentrate to a residue. Purify by flash chromatography, eluting with hexanes/ethyl acetate (10/2) to give the title compound (7 mg). MS (APCI) m/z (35Cl) 379.3 (M+1)+.

Workup

  1. stirringStir 30 min
  2. temperaturewarm
  3. customthe reaction slowly to room temperature
  4. customthe reaction
  5. waitto continue overnight
  6. customQuench
  7. customthe reaction
  8. extractionextract with ethyl acetate
  9. dry with materialdry over sodium sulfate
  10. filtrationfilter
  11. concentrationconcentrate to a residue
  12. customPurify by flash chromatography
  13. washeluting with hexanes/ethyl acetate (10/2)

Sources & evidence

ORD record
ord-e3450ec115254cdf9a011e7d9dbacd0e
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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