Methanol → 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine carboxylic acid

HRID 2200911Notes

Reaction equation

HRID 2200911 reaction equation
CO.[Cl:3][C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:7][NH:8][C:9]1[C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][N:12]=[C:11]([N:20]2[CH2:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[CH2:21]2)[N:10]=1.O.[Na]>O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:7][NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]([N:20]2[CH2:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[CH2:21]2)[N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 71353970Sodium monohydrateHCID 118157304ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6 (7H)yl)-5-pyrimidine carboxylate

Product 1

HCID 1181575174-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine carboxylic acidYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (30 mL) was added in ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6 (7H)yl)-5-pyrimidine carboxylate (3.0 g, 6.82 mmol). Sodium hydrate (0.55 g, 13.6 mmol) was dissolved in water (10 mL) and added into the solution. The reaction was conducted in an oil bath of 50 to 60° C. overnight. LC-MS was used to monitor the reaction. The organic solvent was removed by rotary evaporation. The residual aqueous phase was adjusted to a pH of 3 to 4. Solid was precipitated, filtrated, and dried (1.0 g, 36.0% yield).

Workup

  1. additionadded into the solution
  2. customthe reaction
  3. customThe organic solvent was removed by rotary evaporation
  4. customSolid was precipitated
  5. filtrationfiltrated
  6. customdried (1.0 g, 36.0% yield)

Sources & evidence

ORD record
ord-5b466397233f46b5ab3300ebb64ad871
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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