Phosphorus oxychloride → Ethyl 3-(4-Chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionate

HRID 129008

Reaction equation

HRID 129008 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][CH3:10])[NH:5][C:4](=O)[C:3]=1[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:4]1[C:3]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]([CH3:1])[N:7]=[C:6]([CH2:8][O:9][CH3:10])[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136067006Ethyl 3-(6-Methyl-2-methoxymethyl-3H-pyrimidin-4-on-5-yl)propionate

Product 1

HCID 19372999Ethyl 3-(4-Chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionateYield 84%

Procedure

A mixture of ethyl 3-(6-methyl-2-methoxymethyl-3H-pyrimidin-4-on-5yl)propionate (4.00 g, 15.6 mmol) and phosphorus oxychloride (25 mL) was heated under reflux for 2 h. The mixture was concentrated, cooled, and poured onto ice. 1N NaOH was added to bring the pH to 6 and the mixture was extracted with EtOAc. The extracts were dried (MgSO4) and concentrated to give 3.6 g (84%) of product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. temperaturecooled
  5. additionpoured onto ice
  6. addition1N NaOH was added
  7. extractionthe mixture was extracted with EtOAc
  8. dry with materialThe extracts were dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c6880a16509d4865bfbafe2f1f73db59
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Linked notes

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