HCID 15591933, compound → HCID 15591934, compound

HRID 1248369Notes

Reaction equation

HRID 1248369 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH:9][CH2:10][CH:11]2[CH2:13][C:12]2([Cl:15])[Cl:14])[N:3]=1.[C:16](O)(=[O:18])C.C(OC=O)=O>C(#N)C>[CH:16]([NH:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH:9][CH2:10][CH:11]2[CH2:13][C:12]2([Cl:14])[Cl:15])[N:3]=1)=[O:18]

Participants

4

Reactant 2

HCID 15591933HCID 15591933, compoundHCID 86740153HCID 86740153, compound

Product 1

HCID 15591934HCID 15591934, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2.7 g (0.01 mol) of 2-amino-4-chloro-6-{[(2,2-dichloro-cyclopropyl)methyl]amino}pyrimidine in 300 ml of acetonitrile was added dropwise, while stirring, at room temperature over a period of 15 minutes to a solution of 0.9 gm (0.012 mol) of acetic acid-formic acid anhydride in 5 ml of acetonitrile. After stirring the mixture for about 30 hours at room temperature the solvent was distilled off in vacuo, and the residue was treated twice by dissolving it in about 30 ml of toluene and then distilling the toluene off again. The raw product was purified by column chromatography (150 gm silica gel; eluant: Diisopropyl ether/ethyl acetate 9:1), yielding the title compound as white crystals.

Workup

  1. distillationwas distilled off in vacuo
  2. additionthe residue was treated twice
  3. dissolutionby dissolving it in about 30 ml of toluene
  4. distillationdistilling the toluene off again
  5. customThe raw product was purified by column chromatography (150 gm silica gel; eluant: Diisopropyl ether/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-dfff6a95e9d64e34bc4449bdac0cffe5
Source dataset
uspto-grants-1985_06
Patent number
US04523945

Reaction notes

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