Acetic Acid → 3-benzyl-2-(biphenyl-4-ylmethyl)-7-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1465983

Reaktionsgleichung

C(O)(=O)C.[C:5]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:10]=[CH:9][C:8]([CH:11]=[N:12][NH:13][C:14]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:18](=[O:29])[N:17]([CH3:30])[C:16](=[O:31])[CH:15]=2)=[CH:7][CH:6]=1.N1CCCCC1.[C:44]1([CH2:50][CH:51]=O)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C>[CH2:50]([C:51]1[N:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:10][CH:9]=2)[N:13]=[C:14]2[C:15]=1[C:16](=[O:31])[N:17]([CH3:30])[C:18](=[O:29])[N:19]2[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Komponenten

Reaktionsbedingungen

Temperatur: 42.5 °C

Versuchsvorschrift

Acetic acid (4.4 mL) is added in to a solution of 6-(2-(Biphenyl-4-ylmethylene)hydrazinyl)-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (3.2 g, 7.26 mmol) in DMF (50 mL) and ButOH (25 mL) at 50° C. Piperidine (8.7 mL) is mixed with a solution of 2-phenylacetaldehyde (8.5 mL, 72.6 mmol) in DMF (20 mL), and the resulting greenish solution is added in to the above solution. The reaction mixture is stirred at 40-45° C. for 36 hours under argon, and the solvent is evaporated under high vacuum. The residue is treated with MeOH (200 mL) to precipitate out 1.23 g product as sandy solids (Yield: 31.4%). MS (FAB) m/z 543.4 [M+H]+.

Aufarbeitung

additionthe resulting greenish solution is added in to the above solution
customthe solvent is evaporated under high vacuum
additionThe residue is treated with MeOH (200 mL)

Quellen und Nachweise

ORD-Eintrag: ord-03b47eff05d945b381a4386b59f35338
Quelldatensatz: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09000001B2

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