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

HRID 1470269Notes

Reaction equation

HRID 1470269 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-fa205cfe302c4bba998c7d45673663a6
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

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