Sodium Hydroxide → HCID 136352180, compound

HRID 1631568Notes

Reaction equation

HRID 1631568 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 20 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 20 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-f30db85d1c484253ba445b1dfd394782
Source dataset
uspto-grants-2014_07
Patent number
US08791255B2

Reaction notes

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