Sodium Methoxide → 3-(3-(5-((2-fluoro-4-iodophenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2H)-yl)phenyl) propanamide

HRID 1487157Notes

Reaction equation

HRID 1487157 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]([CH3:33])[C:16](=[O:32])[C:17]([CH3:31])=[C:18]([NH:19][C:20]3[CH:21]=[C:22]([CH2:26][CH2:27][C:28]([NH2:30])=[O:29])[CH:23]=[CH:24][CH:25]=3)[C:13]=2[C:12](=[O:34])[N:11]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[C:10]1=[O:44].C[O-].[Na+]>C1COCC1>[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]([CH3:33])[C:16](=[O:32])[C:17]([CH3:31])=[C:18]2[C:13]=1[C:12](=[O:34])[N:11]([CH2:35][C:36]1[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=1)[C:10](=[O:44])[N:19]2[C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][C:28]([NH2:30])=[O:29])[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 898161213-(3-((1-(2-Fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl)amino)phenyl) propanamide

Product 1

HCID 898280783-(3-(5-((2-fluoro-4-iodophenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2H)-yl)phenyl) propanamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-((1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl)amino)phenyl) propanamide (1b) (1.7 gm, 2.396 mmol) in THF (8 ml) was added sodium methoxide (30% solution in MeOH) (0.431 mg, 2.396 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hr and quenched by addition of 2N HCl solution. The resulting mixture was concentrated under vacuum and residue was re-crystallized in IPA, methanol and water to yield the titled compound (1c) (1.5 g, 88%) [m/z=710.20 (M+1)].

Workup

  1. customquenched by addition of 2N HCl solution
  2. concentrationThe resulting mixture was concentrated under vacuum and residue
  3. customwas re-crystallized in IPA

Sources & evidence

ORD record
ord-d8fab25a692f4545a7f56cb09779acb7
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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