Hydrochloric Acid → HCID 11784741, compound

HRID 1159665Notes

Reaction equation

HRID 1159665 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11]C)=[O:10])=[C:6]([N:13]([CH3:15])[CH3:14])[N:5]=[C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH3:24])=[CH:19][CH:18]=2)[N:3]=1.[OH-].[Na+].CCOCC.Cl>C1COCC1>[Cl:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=[O:10])=[C:6]([N:13]([CH3:14])[CH3:15])[N:5]=[C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH3:24])=[CH:19][CH:18]=2)[N:3]=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-0281d74ffad04c629f7608bf25f91a2c
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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