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Triethylamine → [6-(3-Hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amine

HRID 1452623
Notes
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Reaction equation

HRID 1452623 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6](Cl)[N:5]2[N:13]=[CH:14][CH:15]=[C:4]2[N:3]=1.C(N(CC)CC)C.[CH3:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1>C(O)(C)C>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH3:23])=[CH:27][CH:28]=2)[N:5]2[N:13]=[CH:14][CH:15]=[C:4]2[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90764-EthoxyanilineHCID 575268493-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)propan-1-ol

Product 1

HCID 57526854[6-(3-Hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amineYield 67.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

To an isopropanol (3 mL) solution containing 3-(5,7-dichloropyrazolo[1,5-a]pyrimidin-6-yl)propan-1-ol (224 mg, 0.910 mmol), triethylamine (253 μL, 1.82 mmol) and phenethidine (128 μL, 1.00 mmol) were added, and this mixture was stirred at 40° C. for 5 hr. After the reaction, the solvent was distilled off, aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the filtrate was concentrated and the residue was purified with column chromatography (30% ethyl acetate-hexane) to obtain the title compound (212 mg).

Workup

  1. additionwere added
  2. customAfter the reaction
  3. distillationthe solvent was distilled off
  4. additionaqueous sodium hydrogen carbonate was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate layer was dried over sodium sulfate
  7. filtrationAfter the sodium sulfate was filtered off
  8. concentrationthe filtrate was concentrated
  9. customthe residue was purified with column chromatography (30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c62276d5338a481cb80cd81436d76fe6
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07473694B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes