Methyl Acrylate → (E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-acrylic acid methyl ester

HRID 403481Notes

Reaction equation

Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[C:8]([CH2:18][CH3:19])=[N:9][N:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[N:12][C:11]=23)=[CH:4][CH:3]=1.[C:22]([O:26][CH3:27])(=[O:25])[CH:23]=[CH2:24].C1(N(C2CCCCC2)C)CCCCC1>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:27][O:26][C:22](=[O:25])/[CH:23]=[CH:24]/[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[C:8]([CH2:18][CH3:19])=[N:9][N:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[N:12][C:11]=23)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

3-(4-Bromo-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (3) (525 mg, 1.47 mmol) was dissolved in 15 ml of dioxane and after addition of methyl acrylate (264 ul, 2.93 mmol), dicyclohexyl-methylamine (622 ul ml, 2.93 mmol) and Pd(PtBu3)2 (15 mg, 0.03 mmol) the mixture was heated for 5 min at 130° C. in a microwave oven. Then the mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate, washed with sat. NaHCO3— and NaCl-solution, and dried over Na2 SO4. Evaporation gave a yellow solid. The crude product was purified by recrystallization from diethylether to give a colorless solid.

Workup

customThen the mixture was evaporated under reduced pressure
additionThe residue was diluted with ethyl acetate
washwashed with sat. NaHCO3— and NaCl-solution
customdried over Na2 SO4
customEvaporation
customgave a yellow solid
customThe crude product was purified by recrystallization from diethylether
customto give a colorless solid

Sources & evidence

ORD record: ord-5ba138c63e8a414fbac0e1ce6a081e0d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748435B2

Reaction notes

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