Water → HCID 57978103, compound

HRID 1865914Notes

Reaction equation

HRID 1865914 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[F:13][C:14]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:15]=1[NH2:16].CCN(CC)CC.O>C(Cl)(Cl)Cl>[Cl:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=2[F:13])[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Product 1

HCID 57978103HCID 57978103, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde [Santilli, et al., J. Heterocycl. Chem. 1971, 8, 445-45] (4.0 g, 18.0 mmol) in CHCl3 (50 mL) was added 2,4-di-fluoroaniline (2.02 mL, 19.8 mmol) followed by Et3N (3.76 mL, 27 mmol, 1.5 eq). The reaction mixture turned yellow and was heated to reflux for 6 h, H2O (50 mL) was added and the layers were separated. The organic layer was evaporated to give 6.5 g (>100%) of the crude title compound which is pure enough to be used in the next step. LC MS (m/e)=316 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. customthe layers were separated
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-1f90213df0cd4d9ba69b70247e9d3b33
Source dataset
uspto-grants-2009_12
Patent number
US07629350B2

Reaction notes

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