Ammonia → 2-Amino-4-chloropyrimidine-5-carbonitrile

HRID 525018Notes

Reaction equation

HRID 525018 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[NH3:11]>O1CCOCC1>[NH2:11][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 140269072,4-Dichloro-5-cyanopyrimidine

Product 1

HCID 717413792-Amino-4-chloropyrimidine-5-carbonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2,4-dichloropyrimidine-5-carbonitrile (600 mg, 3.45 mmol) in dioxane (20 ml) was added a 0.5M solution of NH3 in dioxane (20 ml, 10 mmol) and the mixture stirred at room temperature for 4 h. A mixture of two isomers were obtained and separated by column chromatography using a mixture of hexane/ethyl acetate (from 0% to 45% of ethyl acetate). The title compound (304 mg, 56% yield) was found to be the less polar isomer.

Workup

  1. additionA mixture of two isomers
  2. customwere obtained
  3. customseparated by column chromatography
  4. additiona mixture of hexane/ethyl acetate (from 0% to 45% of ethyl acetate)

Sources & evidence

ORD record
ord-3ba2d1a961ca4e4aad6657edb79c207c
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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