Phosphorus oxychloride → Ethyl 3-{4-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate

HRID 657170Notes

Reaction equation

HRID 657170 reaction equation
O[C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][N:5]=[C:4](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][N:5]=[C:4](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178471115HCID 178471115, compound

Product 1

HCID 86635376Ethyl 3-{4-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoateYield 53%

Procedure

Ethyl 3-{4-hydroxy-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate (11.6 g, 38.9 mmol) in POCl3 (30 mL) was heated at 120° C. for 4 h. The solvent was removed in vacuo. The crude residue was then purified by column chromatography (silica gel) using an EtOAc/hexanes (30-50%) gradient to yield the desired compound as a yellow solid (6.6 g, 53%). LCMS (ES+) m/z 317 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude residue was then purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-84c775c75cc842ccbdb816e62935acf3
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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