18-Crown-6 → HCID 23324661, compound

HRID 1380843Notes

Reaction equation

HRID 1380843 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[N:5]=[C:4]([CH2:11][Cl:12])[CH:3]=1.[F-:13].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C.C(OCC)C>[Cl:12][CH2:11][C:4]1[CH:3]=[C:2]([F:13])[N:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[N:5]=1

Participants

6

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 23324650HCID 23324650, compound

Product 1

HCID 23324661HCID 23324661, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.8 g (0.0039 mol) of 6-chloro-4-chloromethyl-2-isopropyl-pyrimidine (see Example 61), 0.51 g (0.0089 mol) of anhydrous potassium fluoride and 0.14 g (0.0004 mol) of 18-crown-6 in 7 ml of acetonitrile is heated at reflux temperature for 48 hours. The mixture is then taken up in diethyl ether and the solution is washed with saturated sodium chloride solution, dried over anhydrous sodium sulphate and freed from solvent under reduced pressure. The 4-chloromethyl-6-fluoro-2-isopropyl-pyrimidine is obtained in the form of a yellow oil, 1H-NMR (CDCl3): 1.32 (d, CH(CH3)2), 3.18 (m, CH(CH3)2), 4.62 (s, CH2Cl), 6.99 (d, CH).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 48 hours
  3. washthe solution is washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record
ord-acd5f09e74ae444d8c55005339d4568c
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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