Sodium Hydroxide → HCID 136346158, compound

HRID 1399766Notes

Reaction equation

HRID 1399766 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:5][C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[C:3]1[CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24]C)=[O:23].[OH-].[Na+]>CO>[O:1]=[C:2]1[NH:7][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:5][C:4]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[C:3]1[CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136346168HCID 136346168, compound

Product 1

HCID 136346158HCID 136346158, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound is prepared according to general method D from methyl 2-(6-oxo-2-(piperidin-1-yl)-4-p-tolyl-1,6-dihydropyrimidin-5-yl)pentanoate (1 eq), sodium hydroxide 10N (10 eq) in methanol (6 mL/mmol) at 60° C. for 18 h. The reaction mixture is concentrated under reduced pressure, the residue is dissolved in water and extracted with diethyl ether. The pH of the aqueous layer is adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N. The suspension is extracted twice with ethyl acetate and the combined organic layers are dried over sodium sulfate and concentrated under reduced pressure to yield the title compound.

Workup

  1. customThis compound is prepared
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with diethyl ether
  5. additionThe pH of the aqueous layer is adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N
  6. extractionThe suspension is extracted twice with ethyl acetate
  7. dry with materialthe combined organic layers are dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f29279e1bae42918269452a488a1797
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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