Sodium Hydroxide → HCID 69068678, compound

HRID 216125Notes

Reaction equation

HRID 216125 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([NH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:14]=[C:13]([O:28][CH3:29])[N:12]=2)[CH:8]=[CH:7][C:6]=1[Cl:30])C.[OH-].[Na+]>CO.O>[ClH:30].[Cl:30][C:6]1[CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[C:15]([NH:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[N:14]=[C:13]([O:28][CH3:29])[N:12]=2)=[CH:10][C:5]=1[C:4]([OH:31])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11619108HCID 11619108, compound

Product 1

HCID 69068678HCID 69068678, compoundYield 166.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-chloro-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid ethyl ester [120 mg, 0.27 mmol, Example 35(z)] and sodium hydroxide (2 mL, 4 mmol, 2M) in MeOH (8 mL) and water (2 mL) is stirred for 15 hours at 60° C. The mixture is concentrated, and diluted with water and ethyl acetate. The mixture is acidified with dilute hydrochloric acid to pH, 3, and extracted with ethyl acetate. The combined extracts are dried over magnesium sulfate, filtered, and concentrated. The residue is treated with saturated hydrogen chloride in EtOAc and concentrated to afford 2-chloro-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid hydrochloride salt [101 mg, 82%, Example 23(e)]. LCMS: RT=2.47 minutes, MS: 414 (M+H).

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water and ethyl acetate
  3. extraction3, and extracted with ethyl acetate
  4. dry with materialThe combined extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe residue is treated with saturated hydrogen chloride in EtOAc
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a2cd6b4e590a4b0f8166e1182d9869d8
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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