N,N-Dimethylaniline → HCID 86653834, compound

HRID 2364914Notes

Reaction equation

HRID 2364914 reaction equation
[Br:1][C:2]1[C:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:4][C:5](O)=[N:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:32])=O>>[Br:1][C:2]1[C:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:4][C:5]([Cl:32])=[N:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178442491HCID 178442491, compound

Product 1

HCID 86653834HCID 86653834, compoundYield 99.3%

Conditions

Temperature
100 °C

Procedure

To 19.6 g (57.1 mmol) of 5-bromo-4,6-dihexylpyrimidin-2-ol was added 2.8 g (23 mmol) of N,N-dimethylaniline, and 40.8 g (266 mmol) of phosphoryl chloride was added under a nitrogen atmosphere, and the mixture was stirred at 100° C. for 2 hours. The resultant mixed liquid was cooled down to room temperature, then, 200 g of ice water was added, and the mixture was extracted with MTBE, washed with water and saturated saline in this order, dried over magnesium sulfate and concentrated. The resultant concentrate was purified by a silica gel column (hexane•ethyl acetate) to obtain 20.5 g (56.7 mmol) of 5-bromo-2-chloro-4,6-dihexylpyrimidine represented by the following formula:

Workup

  1. additionwas added under a nitrogen atmosphere
  2. additionThe resultant mixed liquid
  3. temperaturewas cooled down to room temperature
  4. extractionthe mixture was extracted with MTBE
  5. washwashed with water and saturated saline in this order
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. concentrationThe resultant concentrate
  9. customwas purified by a silica gel column (hexane•ethyl acetate)

Sources & evidence

ORD record
ord-45a7bae54c7a4afbae997b14b7e26dbd
Source dataset
uspto-grants-2014_04
Patent number
US08697256B2

Reaction notes

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