Sodium Hydroxide → HCID 136352180, compound

HRID 880074Notes

Reaction equation

HRID 880074 reaction equation
[OH-].[Na+].[N:3]1([C:9]2[N:10]=[C:11]([CH2:16][C:17]([NH:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([O:25]C)=[O:24])=[O:18])[NH:12][C:13](=[O:15])[CH:14]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1>CO>[N:3]1([C:9]2[N:10]=[C:11]([CH2:16][C:17]([NH:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([OH:25])=[O:24])=[O:18])[NH:12][C:13](=[O:15])[CH:14]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136041736HCID 136041736, compound

Product 1

HCID 136352180HCID 136352180, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1.8 ml of 2 M sodium hydroxide are added to a solution of 335 mg of methyl 3-({[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetyl}amino)-benzoate in 25 ml of methanol. The reaction mixture is heated at 60° C. for 2 h 30, and it is then concentrated under reduced pressure. The evaporation residue is taken up in 50 ml of water. The aqueous phase is extracted with ethyl acetate and then acidified (pH=6) by adding a 1N solution of hydrochloric acid. The precipitate formed is filtered off and then washed with ml of water, 5 ml of ethyl acetate and, finally, 20 ml of ethyl ether. The solid is dried under vacuum and 175 mg of 3-({[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetyl}amino)benzoic acid are thus obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. concentrationis then concentrated under reduced pressure
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. additionby adding a 1N solution of hydrochloric acid
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with ml of water, 5 ml of ethyl acetate
  7. dry with materialThe solid is dried under vacuum and 175 mg of 3-({[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetyl}amino)benzoic acid
  8. customare thus obtained in the form of a white solid

Sources & evidence

ORD record
ord-d5fcea2f8fd2478fb186c839c3fce8fe
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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