Sodium Hydroxide → HCID 11582418, compound

HRID 1161661Notes

Reaction equation

HRID 1161661 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:10]=[C:9]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([Cl:30])[CH:23]=2)[N:8]=1)C.[OH-].[Na+]>CO>[Cl:30][C:24]1[CH:23]=[C:22]([NH:21][C:9]2[N:8]=[C:7]([O:6][CH2:5][C:4]([OH:31])=[O:3])[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)[N:10]=2)[CH:27]=[CH:26][C:25]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11655185HCID 11655185, compound

Product 1

HCID 11582418HCID 11582418, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of [2-(3-chloro-4-methoxyphenylamino)-6-(4-methoxyphenyl)pyrimidin-4-yloxy]acetic acid ethyl ester (0.15 g, 0.33 mmol) in MeOH (5 mL) was added aqueous NaOH (prepared by adding NaOH in 2 mL of water) and the mixture was stirred for 3 hours at refluxing temperature. The mixture was then cooled to temperature in the range of 20-40° C., concentrated under vacuum, diluted with water (5 mL) and washed with ethyl acetate (2 x 2 mL). The aqueous layer was neutralized with 2N HCl. The solid precipitated was filtered off and dried to give the desired compound.

Workup

  1. temperatureat refluxing temperature
  2. concentrationconcentrated under vacuum
  3. additiondiluted with water (5 mL)
  4. washwashed with ethyl acetate (2 x 2 mL)
  5. customThe solid precipitated
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-2dc49d206c214b1fa89ba8bc52ec3827
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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