Sodium Hydroxide → HCID 11532199, compound

HRID 2110652Notes

Reaction equation

HRID 2110652 reaction equation
C([O:3][C:4](=[O:34])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[C:19]([NH:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[N:18]=[C:17]([O:32][CH3:33])[N:16]=2)[CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>CO.C1COCC1.O>[CH3:33][O:32][C:17]1[N:16]=[C:15]([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:34])=[O:3])[CH:20]=[C:19]([NH:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[N:18]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 69063981HCID 69063981, compound

Product 1

HCID 11532199HCID 11532199, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenoxy)-2-methyl-propionic acid ethyl ester [330 mg, 0.7 mmol, Example 22(a)] in a 2 M solution of sodium hydroxide (5 mL, 10 mmol) in MeOH (4 mL), THF (2 mL) and water (4 mL) is heated to 60° C. for 30 minutes. After an additional 5 hours at room temperature, the mixture is concentrated, and diluted with water and ethyl acetate. The solution is acidified with dilute hydrochloric acid to pH, 2.0, and extracted with ethyl acetate. The extracts are dried over magnesium sulfate, filtered, and concentrated to afford 2-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenoxy)-2-methyl-propionic acid [0.21 g, 72%, Example 23(a)]. LCMS: RT=2.47 minutes, MS: 438 (M+H).

Workup

  1. concentrationthe mixture is concentrated
  2. additiondiluted with water and ethyl acetate
  3. extraction2.0, and extracted with ethyl acetate
  4. dry with materialThe extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a9284de60970411fbab21e365424217f
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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