Isopropanol → (6-Allyl-5-chloropyrazolo[1,5-a]pyrimidin-7-yl)(4-ethoxyphenyl)amine

HRID 1452622Notes

Reaction equation

C(O)(C)C.[CH2:5]([C:8]1[C:9]([Cl:18])=[N:10][C:11]2[N:12]([N:15]=[CH:16][CH:17]=2)[C:13]=1Cl)[CH:6]=[CH2:7].[CH3:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1>C(N(CC)CC)C>[CH2:5]([C:8]1[C:9]([Cl:18])=[N:10][C:11]2[N:12]([N:15]=[CH:16][CH:17]=2)[C:13]=1[NH:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH3:19])=[CH:23][CH:24]=1)[CH:6]=[CH2:7]

Participants

Conditions

Temperature: 40 °C

Procedure

To an isopropanol (52 mL) solution containing 6-allyl-5,7-dichloropyrazolo[1,5-a]pyrimidine (5.98 g), triethylamine (12.7 mL) and phenethidine (4.30 g) were added, and this mixture was stirred at 40° C. for 5 hr. After the reaction, the solvent was distilled off. Saturated 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 to obtain the title compound (8.62 g).

Workup

additionwere added
customAfter the reaction
distillationthe solvent was distilled off
additionSaturated aqueous 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

Sources & evidence

ORD record: ord-f59e88fd31274ea4be9ce626c26fb574
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473694B2

Reaction notes

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