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

HRID 2405987Notes

Reaction equation

HRID 2405987 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-319236741c2f4ea6aabfa6cd4cc294c3
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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