Carbon Dioxide → 6-(2-(Biphenyl-4-ylmethylene)hydrazinyl)-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione

HRID 2389528Notes

Reaction equation

HRID 2389528 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)=O.[NH:18]([C:20]1[N:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:24](=[O:35])[N:23]([CH3:36])[C:22](=[O:37])[CH:21]=1)[NH2:19]>CCOC(C)=O>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=[CH:13][C:10]([CH:11]=[N:19][NH:18][C:20]2[N:25]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:24](=[O:35])[N:23]([CH3:36])[C:22](=[O:37])[CH:21]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 667954896-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 667958906-(2-(Biphenyl-4-ylmethylene)hydrazinyl)-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dioneYield 80.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-phenylbenzaldehyde (395 mg, 2.17 mmol) in EtOAc is slowly added into a dry ice cooled slurry of 6-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (200 mg, 0.724 mmol) in EtOAc. After the addition, the reaction mixture is stirred at room temperature for 2 hours. The solvent is evaporated under reduced pressure, and the residue is triturated with MeOH, followed by filtration to give 256 mg product as pale yellow solids (Yield: 80.3%). 1H NMR (400 MHz, DMSO-d6) δ 3.17 (s, 3H), 3.71 (s, 3H), 5.22 (s, 2H), 5.59 (s, 1H), 6.91 and 7.21 (AB, J=7.2 Hz, 4H), 7.37-7.81 (m, 9H), 8.36 (s, 1H), 10.67 (s, 1H). MS (FAB) m/z 441.4 [M+H]+.

Workup

  1. additionAfter the addition
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is triturated with MeOH
  4. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-649888dbd5314c6b95ad8d75bfaef56d
Source dataset
uspto-grants-2012_09
Patent number
US08273750B2

Reaction notes

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