Phosphorus oxychloride → (E)-4-chloro-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidine

HRID 431239Notes

Reaction equation

HRID 431239 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[N:15]=[C:14](O)[CH:13]=[C:12]([CH3:17])[N:11]=2)[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:14]1[CH:13]=[C:12]([CH3:17])[N:11]=[C:10](/[CH:9]=[CH:8]/[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429310HCID 178429310, compound

Product 1

HCID 18763616(E)-4-chloro-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidineYield 71%

Conditions

Temperature
130 °C

Procedure

0.246 g (1 mmol) of (E)-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol were treated with 1.83 ml (20 mmol) of POCl3 and subsequently heated at 130° C. for 4.5 hours. The mixture was cooled to RT, concentrated in vacuo and the residue was partitioned between EtOAc, water and saturated KHCO3. The organic layer was separated, dried over sodium sulphate and concentrated in vacuo. The residue was applied to a short silica gel column with CH2Cl2/hexane (3:2) as eluent. Combination of the purified fractions and concentration in vacuo gave 188 mg (71%) of the desired (E)-4-chloro-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidine as a white solid. EI mass spectrum, m/e: 264 (M calculated for C13H10Cl2N2: 264)

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated in vacuo
  3. customthe residue was partitioned between EtOAc, water and saturated KHCO3
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-e215b00b31a64ae995d7b2246b18ddfb
Source dataset
uspto-grants-2003_12
Patent number
US06657060B2

Reaction notes

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