Sodium Hydroxide → 2-chloro-N-(4,6-dimethoxy-5-pyrimidinyl)-N-(1-(1-pyrazolyl)ethyl)acetamide

HRID 1906695Notes

Reaction equation

HRID 1906695 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:7]([O:14][CH3:15])=[N:8][CH:9]=[N:10][C:11]=1[O:12][CH3:13])=[O:4].[OH-].[Na+].Cl.Cl[CH:20]([N:22]1[CH:26]=[CH:25][CH:24]=[N:23]1)[CH3:21]>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:5]([C:6]1[C:11]([O:12][CH3:13])=[N:10][CH:9]=[N:8][C:7]=1[O:14][CH3:15])[CH:20]([N:22]1[CH:26]=[CH:25][CH:24]=[N:23]1)[CH3:21])=[O:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15585336N-(4,6-dimethoxypyrimidin-5-yl)chloroacetamideHCID 20210169N-(1-chloroethyl)pyrazole hydrochloride

Product 1

HCID 138250972-chloro-N-(4,6-dimethoxy-5-pyrimidinyl)-N-(1-(1-pyrazolyl)ethyl)acetamideYield 37.9%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a 500 ml eggplant-shaped flask equipped with a stirrer, 17.4 g (75.1 mmoles) of 2-chloro-N-(4,6-dimethoxy-5-pyrimidinyl)acetamide was dissolved in 300 ml of dichloromethane, and 5.22 g of benzyl tributyl ammonium chloride was added. Under ice cooling, 41.5 ml of a 50% aqueous solution of sodium hydroxide was added to the mixture with stirring. Thereafter, a solution of 13.8 g (82.6 mmoles) of N-(1-chloroethyl)pyrazole hydrochloride in 70 ml of dichloromethane was added dropwise over about 30 minutes. The mixture was stirred further at room temperature for 2 hours. The reaction mixture was washed with water, dried and concentrated. The resulting solid was recrystallized from isopropanol to give 9.26 g of 2-chloro-N-(4,6-dimethoxy-5-pyrimidinyl)-N-(1-(1-pyrazolyl)ethyl)acetamide as a pale yelllow solid which had the following properties.

Workup

  1. customIn a 500 ml eggplant-shaped flask equipped with a stirrer
  2. stirringThe mixture was stirred further at room temperature for 2 hours
  3. washThe reaction mixture was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-10b58830dafd48c0b6e449fd8a9669a0
Source dataset
uspto-grants-1987_03
Patent number
US04654074

Reaction notes

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