Sodium Hydroxide → HCID 11532199, compound

HRID 216124Notes

Reaction equation

HRID 216124 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 2M 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-577134dd80a4478ba634bb604321877c
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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