Lithium Hydroxide → (2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid

HRID 528456Notes

Reaction equation

HRID 528456 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[C:8]([Cl:20])=[N:9][C:10]([Cl:19])=[N:11][C:12]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)C.[Li+].[OH-]>C1COCC1.O>[Cl:19][C:10]1[N:9]=[C:8]([Cl:20])[C:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])=[C:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[N:11]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86711735(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid ethyl ester

Product 1

HCID 86711742(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid ethyl ester (581 mg, 1.73 mmol) in THF (10 mL) and water (2.5 mL) was added LiOH (951 μL, 1.90 mmol, 2M aqueous solution) and the resulting mixture stirred at RT for 2.5 hours. The reaction mixture was quenched with 1M HCl and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo affording (2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid as a white solid (515 mg, 97%). 1H NMR (400 MHz, CDCl3): δ 4.59 (2H, s), 3.93-3.87 (4H, m), 3.81-3.75 (4H, m).

Workup

  1. customThe reaction mixture was quenched with 1M HCl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13bf2c9d22bd499c839a9cabd05a1f83
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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