Sodium Bicarbonate → HCID 86704184, compound

HRID 333989Notes

Reaction equation

HRID 333989 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9][C:10]#[CH:11])=[C:4]([Cl:12])[N:3]=1.[C:13]([O-:16])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:9]([C:5]1[C:6]([Cl:8])=[N:7][C:2]([NH:1][CH:13]=[O:16])=[N:3][C:4]=1[Cl:12])[C:10]1[CH:10]=[CH:9][CH:5]=[CH:4][CH:11]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 13369447HCID 13369447, compound

Product 1

HCID 86704184HCID 86704184, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A flask was filled with 2.02 g (10 mmol) of 2-amino-4,6-dichloro-5-(prop-2-yn-1-yl)pyrimidine and 10 ml of 2 mol·l1 (20 mmol) of a solution of the Vilsmeier-Haack-Arnold reagent in chloroform. The reaction mixture was refluxed for eight hours. Having been cooled to laboratory temperature, the reaction mixture was poured onto ice and rapidly neutralized by NaHCO3. The obtained mixture was quickly transferred into a separatory funnel and immediately extracted by 3×20 ml of chloroform. The organic fractions were connected and dried using MgSO4. According to TLC, the reaction mixture contained another substance besides 4,6-dichloro-2-{[(dimethylamino)methylene]amino}-5-(prop-2-yn-1-yl)pyrimidine. The acquired mixture was therefore separated by column chromatography with a hexane/ethyl-acetate mobile phase (80/20 to 50/50). After evaporation of the organic solvents, the isolated substances were 686 mg of 4,6-dichloro-2-{[(dimethylamino)methylene]amino}-5-(prop-2-yn-1-yl)pyrimidine, 317 mg of 4,6-dichloro-2-formamido-5-(prop-2-yn-1-yl)pyrimidine and 458 mg of 4,6-dichloro-5-(2-chloroallyl)-2-formamidopyrimidine, which is created by the addition of hydrochloric acid (developed during the reaction) to the triple bond present. The hydrolysis to 2-formamido derivatives did not occur until during the chromatography.

Workup

  1. temperatureThe reaction mixture was refluxed for eight hours
  2. temperatureHaving been cooled to laboratory temperature
  3. additionthe reaction mixture was poured onto ice
  4. customThe obtained mixture was quickly transferred into a separatory funnel
  5. extractionimmediately extracted by 3×20 ml of chloroform
  6. customdried
  7. customThe acquired mixture was therefore separated by column chromatography with a hexane/ethyl-acetate mobile phase (80/20 to 50/50)
  8. customAfter evaporation of the organic solvents
  9. additionis created by the addition of hydrochloric acid (
  10. customdeveloped during the reaction) to the triple bond present

Sources & evidence

ORD record
ord-05a6bf2eef9e487bbc74f5e9c70612f3
Source dataset
uspto-grants-2014_11
Patent number
US08883798B2

Reaction notes

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