4-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde → HCID 68859265, compound

HRID 1783549

Reaction equation

HRID 1783549 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[NH2:12].[CH2:13]([NH:15][C:16]1[C:21]([CH:22]=O)=[CH:20][N:19]=[C:18]([S:24][CH3:25])[N:17]=1)[CH3:14]>C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[N:12]=[CH:22][C:21]1[C:16]([NH:15][CH2:13][CH3:14])=[N:17][C:18]([S:24][CH3:25])=[N:19][CH:20]=1

Participants

5

Reactant 2

HCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehydeHCID 227430742-Chloro-3,5-Dimethoxyaniline

Product 1

HCID 68859265HCID 68859265, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

Into a solution of 3.78 g (20.2 mmol) of 2-chloro-3,5-dimethoxy-phenylamine in 110 mL of toluene was added 3.97 g (20.15 mmol) of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde. The reaction vessel was equipped with a Dean-Stark trap, and the reaction was warmed to reflux. After 3 hours, two drops of concentrated sulfuric acid were added to the reaction. The reaction was refluxed overnight then concentrated in vacuo to give 7.36 g (93%) of the title compound, which was used as is in the following example:

Workup

  1. customThe reaction vessel was equipped with a Dean-Stark trap
  2. temperaturethe reaction was warmed to reflux
  3. temperatureThe reaction was refluxed overnight
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-5db665303cbf4edca956a9ab3e11c1fe
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Linked notes

Loading…