Hydrazine hydrate (1:1) → HCID 18520588, compound

HRID 1368775Notes

Reaction equation

HRID 1368775 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:18])[N:3]=1.O.[NH2:20][NH2:21]>O1CCCC1>[Cl:18][C:4]1[CH:5]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:7]=[C:2]([NH:20][NH2:21])[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 132301362,6-Dichloro-N-[(4-methoxyphenyl)methyl]pyrimidin-4-amine

Product 1

HCID 18520588HCID 18520588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 5.57 g portion of 2,6-dichloro-4-(4-methoxybenzyl)aminopyrimidine was suspended in 20 ml of tetrahydrofuran, mixed with 3.0 ml of hydrazine monohydrate and heated under reflux for 24 hours. After evaporation of the solvent under a reduced pressure, water was added to the residue and the resulting precipitate was collected by filtration to obtain 5.06 g of 4-chloro-2-hydrazino-6-(4-methoxybenzyl)aminopyrimidine as a white solid. This was suspended in 150 ml of ethanol and mixed with 3.37 g of ethoxymethyleneacetoacetic acid ethyl ester at room temperature, and the mixture was stirred for 1 hour and then heated under reflux for 15 hours. By concentrating the reaction solution to dryness under a reduced pressure, 7.22 g of the title compound was obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. customAfter evaporation of the solvent under a reduced pressure, water
  4. additionwas added to the residue
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-26fe75dff01e4bba802b181877b6cd37
Source dataset
uspto-grants-2003_06
Patent number
US06573377B1

Reaction notes

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