Ethanol → 2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid

HRID 2200905Notes

Reaction equation

HRID 2200905 reaction equation
O.C(O)C.[CH:5]12[CH2:10][CH:9]1[CH2:8][N:7]([C:11]1[N:16]=[C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([F:27])[CH:20]=3)[C:14]([C:28]([O:30]CC)=[O:29])=[CH:13][N:12]=1)[CH2:6]2.[OH-].[Na+]>C1COCC1>[CH:5]12[CH2:10][CH:9]1[CH2:8][N:7]([C:11]1[N:16]=[C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([F:27])[CH:20]=3)[C:14]([C:28]([OH:30])=[O:29])=[CH:13][N:12]=1)[CH2:6]2

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 118157898Ethyl 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylate

Product 1

HCID 1181574972-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acidYield 41.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the mixture of water (5 mL), ethanol (5 mL) and THF (15 mL) were dissolved ethyl 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylate (1.5 g, 3.9 mmol) and sodium hydroxide (260 mg, 6.5 mmol). The reaction was conducted at ambient temperature for 5 h. The solvent was removed by evaporation, followed by addition of water and washing with DCM. The aqueous phase was adjusted to a pH of 2 with dilute hydrochloric acid, and extracted with DCM. The organic phase was dried over sodium sulfate and concentrated to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid as a faint yellow solid (580 mg, 41.5% yield).

Workup

  1. customThe solvent was removed by evaporation
  2. additionfollowed by addition of water
  3. washwashing with DCM
  4. extractionextracted with DCM
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2053a95a781b45b59eb70b9819f55c13
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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