N,N-Dimethylaniline → 4-Chloro-6-(pyridin-4-yl)pyrimidin-2-amine

HRID 16415

Reaction equation

HRID 16415 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=1.P(Cl)(Cl)([Cl:17])=O.CN(C)C1C=CC=CC=1>>[Cl:17][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178508969HCID 178508969, compound

Product 1

HCID 223242864-Chloro-6-(pyridin-4-yl)pyrimidin-2-amine

Conditions

Temperature
100 °C

Procedure

32 g (170.04 mmol) of the compound (from example XXVIII) are dissolved in 87.1 ml (0.93 mmol) of phosphoryl chloride. 2.80 ml (22.11 mmol) of N,N-dimethylaniline are slowly added dropwise, and the mixture is stirred at 100° C. for one hour. The reaction solution is then stirred at room temperature for another two hours. The phosphoryl chloride is removed under reduced pressure using a rotary evaporator. Water/dichloromethane 9:1 is added to the residue, which is then boiled for 5 minutes. The mixture is then neutralized using saturated sodium bicarbonate solution and the product is filtered off with suction and dried under high vacuum.

Workup

  1. stirringThe reaction solution is then stirred at room temperature for another two hours
  2. customThe phosphoryl chloride is removed under reduced pressure
  3. customa rotary evaporator
  4. additionWater/dichloromethane 9:1 is added to the residue, which
  5. waitis then boiled for 5 minutes
  6. filtrationthe product is filtered off with suction
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-ed8e5fe2b94d43c7a773afc10623e42a
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Linked notes

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