Sodium Hydroxide → HCID 178467457, compound

HRID 542385Notes

Reaction equation

HRID 542385 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[C:8]([NH:9][C:10](=[O:13])[CH2:11][Cl:12])=[C:7]([O:14][CH2:15][CH3:16])[N:6]=[CH:5][N:4]=1.Cl.[NH:19]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[N:20]1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.O>[NH:19]1[CH:23]=[CH:22][C:21]([CH2:24][N:9]([C:8]2[C:3]([N:2]([CH3:17])[CH3:1])=[N:4][CH:5]=[N:6][C:7]=2[O:14][CH2:15][CH3:16])[C:10](=[O:13])[CH2:11][Cl:12])=[N:20]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 20208140N-(4-dimethylamino-6-ethoxypyrimidin-5-yl)-chloroacetamideHCID 178478564HCID 178478564, compound

Product 1

HCID 178467457HCID 178467457, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 12.9 g (0.05 mol) N-(4-dimethylamino-6-ethoxypyrimidin-5-yl)-chloroacetamide and 2 g benzyltriethylammoniumchloride in 150 g of CH2Cl2 are added 8.4 g (0.055 mol) of 1-pyrazolylmethylchloride-hydrochloride. To this mixture are quickly added 25 ml of 40% NaOH, whereby the temperature rises from 18° to 32°. The mixture is then stirred for 2 hours and diluted with water. The organic phase is separated off and dried over Na2SO4. The dried solution is evaporated to give an orange oil that is chromatographed on silica gel with the aid of ethylacetate. The thus obtained yellow oil is dissolved in diethylether and crystallised in a deep-freezer. The title compound is obtained in the form of white crystals of m.p. 112°-114°.

Workup

  1. customrises from 18° to 32°
  2. customThe organic phase is separated off
  3. dry with materialdried over Na2SO4
  4. customThe dried solution is evaporated
  5. customto give an orange oil that
  6. customis chromatographed on silica gel with the aid of ethylacetate
  7. dissolutionThe thus obtained yellow oil is dissolved in diethylether
  8. customcrystallised in a deep-freezer

Sources & evidence

ORD record
ord-ef3746e0b2784720a0954597e16b8c31
Source dataset
uspto-grants-1987_04
Patent number
US04657579

Reaction notes

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