Sodium Hydroxide → HCID 66956120, compound

HRID 1399729Notes

Reaction equation

HRID 1399729 reaction equation
[C:1]([O:5][CH:6]([C:11]1[C:12]([CH3:30])=[N:13][C:14]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>ClCCl.CO>[C:1]([O:5][CH:6]([C:11]1[C:12]([CH3:30])=[N:13][C:14]([N:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[N:15][C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66955902HCID 66955902, compound

Product 1

HCID 66956120HCID 66956120, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a mixture of methyl 2-tert-butoxy-2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)acetate (0.030 g; 0.073 mmol) in a mixture dichloromethane-methanol (10:1) (0.55 ml) was added a solution of sodium hydroxide (2N in methanol) (0.075 ml; 0.150 mmol) and the reaction was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, the residue diluted with water and washed with diethyl ether. The pH of the aqueous layer was adjusted to 2 with a solution of hydrochloric acid 2N and the suspension was extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and concentrated under reduced pressure to furnish 0.020 g (65%) of the title compound as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. washwashed with diethyl ether
  4. extractionthe suspension was extracted twice with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5cfeb31b21a41b496af324e10a172a7
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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