Ammonia → HCID 46882092, compound

HRID 733155Notes

Reaction equation

HRID 733155 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH3:10])[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:3]=1.[Cu][C:22]#[N:23].C(OCC)(=O)C.N>CN1CCCC1=O>[CH2:8]([C:6]1[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:3]=[C:2]([C:22]#[N:23])[N:7]=1)[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 86619631HCID 86619631, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 46882092HCID 46882092, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 2-chloro-4-propyl-6-(3-trifluoromethylphenyl)-pyrimidine (50 mg) in 1-methyl-2-pyrrolidinone (2 mL), was added copper(I) cyanide (60 mg). The suspension was heated in the microwave at 200° C. for 20 min, than poured into a mixture of ethyl acetate (10 mL) and ammonia solution (5 mL). The organic layer was separated, washed with water (10 mL), dried over sodium sulphate and evaporated at reduced pressure. Preparative HPLC afforded the title compound 4-propyl-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile as a brown gum (4.1 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (10 mL)
  3. dry with materialdried over sodium sulphate
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-b4ed5ce7205f4e5e94cd621cd96cfd7b
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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