Dichloromethane → Methyl 3-[4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinyl]-2-propenoate

HRID 1651528Notes

Reaction equation

HRID 1651528 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=O)=[C:12]([CH3:16])[N:11]=[C:10]([CH3:17])[N:9]=2)=[CH:4][CH:3]=1.CC1C([P+]([O:38][C:39]([CH3:41])=[O:40])(C2C=CC=CC=2)C2C=CC=CC=2)=CC=CC=1.Cl[CH2:43]Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[CH:41][C:39]([O:38][CH3:43])=[O:40])=[C:12]([CH3:16])[N:11]=[C:10]([CH3:17])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 145138864-(4-Fluorophenyl)-2,6-dimethyl-5-pyrimidinecarboxaldehydeHCID 53420851Methyl(triphenylphosphoranylidene) acetate

Product 1

HCID 53886596Methyl 3-[4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinyl]-2-propenoate

Procedure

4-(4-Fluorophenyl)-2,6-dimethyl-5-pyrimidinecarboxaldehyde (31 g, 0.134 mol) and methyl(triphenylphosphoranylidene) acetate (46.6 g, 0.139 mol) in 500 mL of dichlormethane were stirred at room temperature for twenty-four hours. The solution was then concentrated and flash chromatographed on silica gel, eluting with 20% ethyl acetate/hexane, to give 36.3 g of methyl 3-[4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinyl]-2-propenoate.

Workup

  1. concentrationThe solution was then concentrated
  2. customflash chromatographed on silica gel
  3. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1aa254e350124dae9833d8be7c7a33fd
Source dataset
uspto-grants-1990_05
Patent number
US04929620

Reaction notes

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