Ammonium Chloride → HCID 10683618, compound

HRID 1281087Notes

Reaction equation

HRID 1281087 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[C:3]=1[CH:12]([CH3:14])[CH3:13].[CH2:15]([Mg]Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>[Ni].O1CCCC1>[CH3:9][O:8][C:6]1[N:5]=[C:4]([O:10][CH3:11])[C:3]([CH:12]([CH3:14])[CH3:13])=[C:2]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 178418336HCID 178418336, compound

Product 1

HCID 10683618HCID 10683618, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

0.15 g of nickel catalyst of expanded formula Ni(Acac)2 is added, in a 0.25 liter three-necked Erlenmeyer flask rendered inert with nitrogen, at a temperature below 5° C. and in one step, to the mixture in solution of 15 g (0.07 mol) of the compound of Example 8, 150 ml of tetrahydrofuran and 34.6 ml (0.07 mol) of a 2M solution of benzylmagnesium chloride in tetrahydrofuran. The medium is brought back to ambient temperature and, at the end of the progression of the coupling, treated by addition of 50 ml of a 10% ammonium chloride solution. The upper organic phase is separated, washed with an additional 50 ml of a 10% ammonium chloride solution and then washed with water. The organic phase is evaporated to dryness in order to obtain an oily residue (boiling temperature under 5 mbar=140-150° C.) which is purified again by chromatography on silica gel, elution being carried out with toluene, in order to result in 3.2 g of 2,4-dimethoxy-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine.

Workup

  1. customis brought back to ambient temperature and, at the end of the progression of the coupling
  2. customThe upper organic phase is separated
  3. washwashed with an additional 50 ml of a 10% ammonium chloride solution
  4. washwashed with water
  5. customThe organic phase is evaporated to dryness in order
  6. customto obtain an oily residue (boiling temperature under 5 mbar=140-150° C.) which
  7. customis purified again by chromatography on silica gel, elution
  8. customto result in 3.2 g of 2,4-dimethoxy-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine

Sources & evidence

ORD record
ord-8821a674ac5d43c38b82bddadf44b07e
Source dataset
uspto-grants-2002_09
Patent number
US06452006B1

Reaction notes

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