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

HRID 1452623Notes

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

Participants

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

additionwere added
customAfter the reaction
distillationthe solvent was distilled off
additionaqueous sodium hydrogen carbonate was added to the residue
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined ethyl acetate layer was dried over sodium sulfate
filtrationAfter the sodium sulfate was filtered off
concentrationthe filtrate was concentrated
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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