Thionyl Chloride → 5-(1-Chloro-butyl)-2-(2,6-diethyl-phenyl)-4-methoxy-6-methyl-pyrimidine

HRID 1455769Notes

Reaction equation

HRID 1455769 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([CH:19](O)[CH2:20][CH2:21][CH3:22])=[C:13]([CH3:24])[N:12]=1)[CH3:2].O=S(Cl)[Cl:27]>C(Cl)Cl>[Cl:27][CH:19]([C:14]1[C:15]([O:17][CH3:18])=[N:16][C:11]([C:4]2[C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:9][CH3:10])=[N:12][C:13]=1[CH3:24])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 665896771-[2-(2,6-Diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]butan-1-ol

Product 1

HCID 665896555-(1-Chloro-butyl)-2-(2,6-diethyl-phenyl)-4-methoxy-6-methyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(2,6-diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]butan-1-ol (1 g, 3 mmol) [prepared as described in Example 10] in dry DCM (20 mL) is added SOCl2 (7 mL 0.015 mol) dropwise under nitrogen. The solution is then allowed to stir at room temperature for 1 h. The reaction mixture is concentrated and azeotroped with toluene twice to obtain 5-(1-chloro-butyl)-2-(2,6-diethyl-phenyl)-4-methoxy-6-methyl-pyrimidine which is used in standard nucleophilic displacement reactions to obtain a variety of compounds including the following:

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customazeotroped with toluene twice

Sources & evidence

ORD record
ord-75ba158a227d4af6bcb96ae65e1bada7
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Reaction notes

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