Hydrochloric Acid → HCID 11784741, compound

HRID 2422153Notes

Reaction equation

HRID 2422153 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[C:6]([Cl:32])=[N:7][C:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[CH3:22])=[CH:17][CH:16]=2)=[N:9][C:10]=1[N:11]([CH3:13])[CH3:12].[OH-].[Na+].CCOCC.Cl>C1COCC1>[Cl:32][C:6]1[C:5]([CH2:4][C:3]([OH:33])=[O:2])=[C:10]([N:11]([CH3:12])[CH3:13])[N:9]=[C:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[CH3:22])=[CH:17][CH:16]=2)[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 59514566HCID 59514566, compound

Product 1

HCID 11784741HCID 11784741, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This crude methyl[4-chloro-2-{4-[(4-chlorobenzoyl)(methyl)amino]benzyl}-6-(dimethyl-amino)pyrimidin-5-yl]acetate was dissolved in THF (3 mL) and treated with 1N NaOH (2 mL) and stirred at room temperature for 24 hour. Et2O was added and the organic phase was siphoned off. The remaining aqueous layer was acidified with 6N HCl to pH˜5 and the separated solids were collected by suction and rinsed with water and diisopropyl ether. Drying under high vacuum at room temperature for 4 hours then gave [4-chloro-2-{4-[(4-chlorobenzoyl)(methyl)amino]-benzyl}-6-(dimethylamino)pyrimidin-5-yl]acetic acid (0.029 g, 27% yield) as a pale yellow powder.

Workup

  1. customthe separated solids were collected by suction
  2. washrinsed with water and diisopropyl ether
  3. customDrying under high vacuum at room temperature for 4 hours

Sources & evidence

ORD record
ord-fd6d57117298475f84ac2e942b7eefe5
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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