N,N-Dimethylaniline → 2,4-Dichloro-6-ethylpyrimidine

HRID 1289495Notes

Reaction equation

HRID 1289495 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)C1C=CC=CC=1.O[C:16]1[N:21]=C(O)[CH:19]=[C:18]([CH2:23][CH3:24])[N:17]=1.Cl[CH2:26][Cl:27]>>[Cl:3][C:16]1[N:21]=[C:26]([Cl:27])[CH:19]=[C:18]([CH2:23][CH3:24])[N:17]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178436953HCID 178436953, compound

Product 1

HCID 2460102,4-Dichloro-6-ethylpyrimidineYield 93.3%

Procedure

A mixture of phosphorous oxychloride(43 ml), N,N-dimethyl aniline(6.6 ml) and 2,4-dihydroxy-6-ethyl pyrimidine(11.12 g, 79.3 mmol) prepared in the above Step 2 was heated to reflux for 6 hours. The reaction mixture was cooled to a room temperature and diluted with dichloromethane. The diluted solution was added slowly to ice water, while maintaining the temperature of the reaction system below 10° C. and the mixture was extracted with dichloromethane. The combined dichloromethane layers were dried over magnesium sulfate and concentrated to give 13.10 g of the titled compound as an oily form. (Yield: 93.3%)

Workup

  1. customprepared in the above Step 2
  2. temperaturewas heated
  3. temperatureto reflux for 6 hours
  4. temperaturewhile maintaining the temperature of the reaction system below 10° C.
  5. extractionthe mixture was extracted with dichloromethane
  6. dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bb746ff477684419b19dd972e8ca2678
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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