Aluminum(III) Chloride → 5-((2-fluoro-4-iodophenyl)amino)-1-(3-(3-hydroxypyrrolidine-1-carbonyl)phenyl)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione

HRID 1487162Notes

Reaction equation

HRID 1487162 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[N:15]([CH3:51])[C:16](=[O:50])[C:17]([CH3:49])=[C:18]2[C:23]=1[C:22](=[O:24])[N:21](CC1C=CC(OC)=CC=1)[C:20](=[O:34])[N:19]2[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([N:43]2[CH2:47][CH2:46][CH:45]([OH:48])[CH2:44]2)=[O:42])[CH:36]=1>C1(OC)C=CC=CC=1>[F:5][C:6]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[N:15]([CH3:51])[C:16](=[O:50])[C:17]([CH3:49])=[C:18]2[C:23]=1[C:22](=[O:24])[NH:21][C:20](=[O:34])[N:19]2[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([N:43]2[CH2:47][CH2:46][CH:45]([OH:48])[CH2:44]2)=[O:42])[CH:36]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 898159705-((2-fluoro-4-iodophenyl)amino)-1-(3-(3-hydroxypyrrolidine-1-carbonyl)phenyl)-3-(4-methoxybenzyl)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione

Product 1

HCID 717317115-((2-fluoro-4-iodophenyl)amino)-1-(3-(3-hydroxypyrrolidine-1-carbonyl)phenyl)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7(1H,3H,6H)-trioneYield 31%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Aluminium chloride (0.887 g, 6.65 mmol) was added in small portions to a solution of crude 5-((2-fluoro-4-iodophenyl)amino)-1-(3-(3-hydroxypyrrolidine-1-carbonyl)phenyl)-3-(4-methoxybenzyl)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione (2d) (0.500 g, 0.665 mmol) in Anisole (5 ml). The resulting reaction mixture was stirred at room temperature for 16 h, which was then quenched by addition of MeOH (15 ml) and 2N HCl (0.5 ml). The resulting mixture was concentrated under vacuum and the residue thus obtained was purified by silica gel column chromatography to yield the titled compound (22) (0.13 g)

Workup

  1. customThe resulting reaction mixture
  2. customwhich was then quenched by addition of MeOH (15 ml) and 2N HCl (0.5 ml)
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customthe residue thus obtained
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-056199626fe94cc38b2fd40f3edc9589
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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