Methanol → 4-[(3-Chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]pyrimidine-5-carboxylic acid

HRID 2200908

Reaction equation

HRID 2200908 reaction equation
CO.[Cl:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[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[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][OH:26])[N:10]=1.O.[Na]>O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]([N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][OH:26])[N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 52348789Ethyl 4-((3-chloro-4-methoxy-phenyl)methylamino)-2-((2S)-2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylateHCID 71353970Sodium monohydrate

Product 1

HCID 671193354-[(3-Chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]pyrimidine-5-carboxylic acidYield 48.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (50 mL) was added in ethyl (s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidine carboxylate (8.75 g, 20.8 mmol). In water (20 mL) was dissolved sodium hydrate (1.66 g, 41.6 mmol), then the aqueous solution was added to the reaction solution. The reaction was conducted in an oil bath of 50 to 60° C. overnight. The reaction was monitored by LC-MS. The organic solvent was removed by rotary evaporation. The residual aqueous phase was adjusted to a pH of 3 to 4. Then solid was precipitated. The precipitation was filtrated and dried to give a solid (3.9 g, 48.1% yield).

Workup

  1. additionthe aqueous solution was added to the reaction solution
  2. customThe organic solvent was removed by rotary evaporation
  3. customThen solid was precipitated
  4. customThe precipitation
  5. filtrationwas filtrated
  6. customdried

Sources & evidence

ORD record
ord-caed84a4441748fb83a08326067543fe
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Linked notes

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