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3-Pentanol → 7-(1-Ethyl-propoxy)-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

HRID 2183535
Notes
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Reaction equation

HRID 2183535 reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])=[C:14]2[N:13]=[C:12]([CH3:28])[CH:11]=1>C1COCC1>[CH2:2]([CH:3]([O:6][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]3[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[C:14]2[N:13]=[C:12]([CH3:28])[CH:11]=1)[CH2:4][CH3:5])[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 224743217-Chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 98842487-(1-Ethyl-propoxy)-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

A solution of 3-pentanol (140 mg, 1.5 mmol) in 1 ml of dry THF was treated with 60% sodium hydride in oil (28 mg, 0.7 mmol) and stirred at room temperature for 10 min. A solution of 7-chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (75 mg, 0.262 mmol) in 1 ml of dry THF was added and the resulting mixture was heated at reflux for 5 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give the crude material. The residue was purified through silica gel column chromatography using 3:7 chcloroform:hexane as eluent to give 75 mg (88%) of the title compound. 1H NMR (CDCl3) ä 7.97(s, 1H), 6.97(s, 2H), 6.03(s, 1H), 4.56(m, 1H), 2.53(s, 3H), 2.32(s, 3H), 2.13(s, 6H), 2.10(m, 4H), 1.09(t, 6H) ppm.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 5 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customto give the crude material
  9. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-867cc18c2d8a4bfab9f340db8e9a94eb
Source dataset
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06900217B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes