Sodium Hydroxide → HCID 136041768, compound

HRID 880118Notes

Reaction equation

HRID 880118 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:30])[CH2:16][C:17]2[NH:18][C:19](=[O:29])[CH:20]=[C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:22]=2)=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO>[F:3][C:4]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:30])[CH2:16][C:17]2[NH:18][C:19](=[O:29])[CH:20]=[C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[N:22]=2)=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 136230236HCID 136230236, compound

Product 1

HCID 136041768HCID 136041768, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.4 ml of 2M sodium hydroxide is added to a solution of 310 mg of methyl 2-fluoro-5-({[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetyl}-amino)benzoate prepared in Example 57, in 7 ml of methanol. After stirring overnight at ambient temperature, a further 0.4 ml of 2M sodium hydroxide is added and the resulting mixture is brought to reflux for 3 hours. After cooling, the reaction mixture is concentrated under reduced pressure. The evaporation residue is taken up with water. The aqueous phase is extracted with ethyl acetate and then acidified with a 1N aqueous solution of hydrochloric acid (pH=5). The insoluble material is filtered off. The filtrate is concentrated under reduced pressure and then taken up with water and a few drops of a 1N aqueous solution of hydrochloric acid. The precipitate formed is filtered off, rinsed with petroleum ether and concentrated to dryness under reduced pressure. 52 mg of 2-fluoro-5-({[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetyl}amino)benzoic acid are obtained in the form of a pale pink solid, the characteristics of which are the following:

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. filtrationThe insoluble material is filtered off
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customThe precipitate formed
  8. filtrationis filtered off
  9. washrinsed with petroleum ether
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-73fe1717eac64d31bb466e017946fddc
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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