Hexane → HCID 14458736, compound

HRID 1651035Notes

Reaction equation

HRID 1651035 reaction equation
Cl.[C:2]1([CH3:18])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[N:14]=[C:13]([C:15]([NH2:17])=[NH:16])[CH:12]=[CH:11][CH:10]=1.C[O-].[Na+].[CH3:22][CH2:23][CH2:24][CH2:25]CC.C(OCC)(=O)C>CO.COC(OC)C(=O)CC>[CH3:25][C:24]1[CH:23]=[CH:22][N:17]=[C:15]([C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([O:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:18])[N:14]=2)[N:16]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 23051377HCID 23051377, compound

Product 1

HCID 14458736HCID 14458736, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 2420211,1-dimethoxybutan-2-oneSolvent

Procedure

To a mixture of 6-o-tolyloxy-2-picoline amidine hydrochloride (3 g) and methanol (100 ml) were added 28% sodium methoxide solution in methanol (3.3 g) and 1,1-dimethoxybutanone (1.9 g). The mixture was heated under refluxing for an hour, and was left to stand at room temperature. The reaction solution was concentrated under reduced pressure, and the residue obtained was subjected to silica gel column chromatography (eluent; n-hexane: ethyl acetate=2:1 in volume) to obtain 4-methyl-2-(6-o-tolyloxy-2-pyridinyl)pyrimidine (2.4 g, yield 76%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for an hour
  3. waitwas left
  4. customto stand at room temperature
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. customthe residue obtained

Sources & evidence

ORD record
ord-b8b47f47bd9b492ebf1058464026954d
Source dataset
uspto-grants-1990_05
Patent number
US04927827

Reaction notes

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