Potassium Carbonate → 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

HRID 1487161Notes

Reaction equation

HRID 1487161 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2[N:15]([CH3:36])[C:16](=[O:35])[C:17]([CH3:34])=[C:18]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([N:28]4[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]4)=[O:27])[CH:21]=3)[C:13]=2[C:12](=[O:37])[N:11]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:10]1=[O:47].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:14]1[N:15]([CH3:36])[C:16](=[O:35])[C:17]([CH3:34])=[C:18]2[C:13]=1[C:12](=[O:37])[N:11]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)[C:10](=[O:47])[N:19]2[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([N:28]2[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]2)=[O:27])[CH:21]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 898160901-(2-fluoro-4-iodophenyl)-5-((3-(3-hydroxypyrrolidine-1-carbonyl)phenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione

Product 1

HCID 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)-trioneYield 90.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(2-fluoro-4-iodophenyl)-5-((3-(3-hydroxypyrrolidine-1-carbonyl)phenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (550 mg, 0.732 mmol) in THF (2 ml) and Methanol (1 ml), was added K2CO3 (202 mg, 1.464 mmol) at RT. The reaction mixture was stirred at room temperature for 3 h under N2 atm. The solvents were evaporated in vacuo and the residue was suspended in dilute HCl (10 ml). The suspension was extracted several times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulphate. The solvent was evaporated in vacuo to afford 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) (500 mg) which was carried forward for the next step without further purification.

Workup

  1. customThe solvents were evaporated in vacuo
  2. extractionThe suspension was extracted several times with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a295f2e1e17440e0b7eeedab16b8f27d
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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