Triethylamine → acetic acid (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylthio)methyl acetate

HRID 1024629Notes

Reaction equation

HRID 1024629 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:10](=[O:25])[C:11]3C=N[N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.ClC1C=CC(N2[C:45](=[O:46])[C:44]3C=NN(C4C=C(C=CC=4)C#N)C=3N=C2C2C=CC(B3[O:68][C:67]([CH3:70])(C)C(C)(C)O3)=CC=2)=CC=1.C([N:75]([CH2:78]C)CC)C.[OH-:80].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[C:10](=[O:25])[C:11]3[N:75]=[CH:78][N:14]([C:17]4[CH:18]=[C:19]([S:23][CH2:24][O:80][C:67](=[O:68])[CH3:70])[CH:20]=[CH:21][CH:22]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[C:45]([OH:46])(=[O:80])[CH3:44]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 247816196-(4-Bromo-phenyl)-5-(4-chloro-phenyl)-1-(3-methylsulfanyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneHCID 578994373-{5-(4-Chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl}-benzonitrile

Product 1

HCID 131731396acetic acid (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylthio)methyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-N-(4-chloro-phenyl)-benzamide (3) used is prepared by the following procedure. To a solution of 4-chloroaniline (1, 66.0 g, 517.0 mmol) and 4-bromobenzoyl chloride (2, 109.0 g, 497.0 mmol) in dichloromethane (1200 mL) is added triethyl amine (83.0 mL, 596.0 mmol). The reaction mixture is then poured into 0.05 N sodium hydroxide solution and the resulted suspension is stirred at rt for 1 h. The solid formed is filtered and washed with water. The resulted white solid is dried under vacuum. The product is used in the next step reaction.

Workup

  1. customThe solid formed
  2. filtrationis filtered
  3. washwashed with water
  4. customThe resulted white solid is dried under vacuum
  5. customThe product is used in the next step reaction

Sources & evidence

ORD record
ord-d2c5ab2edf574ec180f33895ec074231
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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