Sodium Hydroxide → HCID 50997146, compound

HRID 1399716Notes

Reaction equation

HRID 1399716 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([O:17]C)=[O:16])=[C:12]([CH3:22])[N:11]=[C:10]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:9]=2)=[C:4]([F:29])[CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([OH:17])=[O:16])=[C:12]([CH3:22])[N:11]=[C:10]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:9]=2)=[C:4]([F:29])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66956045HCID 66956045, compound

Product 1

HCID 50997146HCID 50997146, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared according to general method D from methyl 2-(4-(4-chloro-2-fluorophenyl)-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.049 g; 0.117 mmol), sodium hydroxide 10N (0.200 mL; 2.00 mmol) in methanol (2 mL) at 60° C. for 18 h. Purification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane, followed by a purification by preparative HPLC (HPLC method 1) furnished 0.009 g (19%) of the title compound as a white solid.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane
  3. customfollowed by a purification by preparative HPLC (HPLC method 1)

Sources & evidence

ORD record
ord-61f769825a7a48c4bc18276f8e3155bd
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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