Ammonia → 6-Chloro-N5-ethyl-4,5-pyrimidinediamine

HRID 1036333Notes

Reaction equation

HRID 1036333 reaction equation
[CH2:1]([NH:3][C:4]1[C:5](Cl)=[N:6][CH:7]=[N:8][C:9]=1[Cl:10])[CH3:2].[NH3:12]>C(O)C>[CH2:1]([NH:3][C:4]1[C:5]([NH2:12])=[N:6][CH:7]=[N:8][C:9]=1[Cl:10])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57899156HCID 57899156, compound

Product 1

HCID 578991686-Chloro-N5-ethyl-4,5-pyrimidinediamineYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl(4,6-dichloropyrimidin-5-yl)amine (0.31 g, 1.61 mmol) and concentrated aqueous ammonia (10 mL) in ethanol (3 mL) was heated to 100° C. in a sealed tube for 16 hours. The solution was cooled and evaporated to dryness. The residue was partitioned between ethyl acetate (20 mL) and dilute brine (10 mL). The organic layer was dried, filtered and concentrated to give N5-ethyl-6-chloropyrimidine-4,5-diamine (0.214 g, 1.24 mmol, 77%) as a waxy solid. LC-MS (LCT2) m/z 173, 175 [M+H+], Rt 3.97.

Workup

  1. temperatureThe solution was cooled
  2. customevaporated to dryness
  3. customThe residue was partitioned between ethyl acetate (20 mL) and dilute brine (10 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c96d1266c9df4f96b9f9cab029f1e5ce
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

Loading…