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 1465983Notes

Reaction equation

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

Participants

Conditions

Temperature: 42.5 °C

Procedure

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]+.

Workup

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)

Sources & evidence

ORD record: ord-03b47eff05d945b381a4386b59f35338
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000001B2

Reaction notes

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