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Chlorosuccinimide → 4-(4-Chloro-5-(2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiazol-2-yl)morpholine

HRID 1660747
Notes
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Reaction equation

HRID 1660747 reaction equation
Br[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[C:8]([CH3:22])=[N:9][N:10]2[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][C:13]([CH3:21])=[N:12][C:11]=12.C([Li])CCC.[Cl:34]N1C(=O)CCC1=O.[Cl-].N>C1COCC1>[Cl:34][C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[C:8]([CH3:22])=[N:9][N:10]2[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][C:13]([CH3:21])=[N:12][C:11]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 31398ChlorosuccinimideHCID 20976574Ammonia chlorideHCID 67428983HCID 67428983, compoundHCID 178418339Butyllithium

Product 1

HCID 248989774-(4-Chloro-5-(2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiazol-2-yl)morpholineYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere dissolve 3-(4-bromo-2-morpholin-4-yl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (116 mg, 0.25 mmol) in THF (1.5 mL) and chill to −78° C. Add n-butyl lithium (0.1 mL. 2.5 M in hexane, 0.25 mmol) and stir at −78° C. for 30 min. Add N-chlorosuccinimide (33.4 mg, 0.25 mmol) and stir for another 30 min, slowly warming to room temperature. After stirring overnight, quench the reaction by adding a solution of saturated ammonia chloride and extract with ethyl acetate. Wash the organic layer with brine, dry over sodium sulfate, filter, and concentrate to a residue. Purify the crude material by flash chromatography, eluting with hexanes:dichloromethane:ethyl acetate (5:5:2) to provide the title compound (54 mg). MS (APCI) m/z (35Cl) 420.6 (M+1)+; 1H NMR (400 MHz, CDCl3): 6.44 (s, 1H), 3.79 (t, 4H, J=4.8 Hz), 3.63-3.56 (m, 1H), 3.47 (t, 4H, J=4.8 Hz), 2.55 (s, 3H), 2.45 (s, 3H), 1.88-1.75 (m, 4H), 0.87 (t, 6H, J=7.5 Hz).

Workup

  1. temperatureslowly warming to room temperature
  2. customquench
  3. customthe reaction
  4. extractionextract with ethyl acetate
  5. washWash the organic layer with brine
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate to a residue
  9. customPurify the crude material by flash chromatography
  10. washeluting with hexanes:dichloromethane:ethyl acetate (5:5:2)

Sources & evidence

ORD record
ord-e6c51a9b595947268f6845f46b1dc5dd
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030304B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes