Water → 6-(2,4-Dichlorophenyl)-2-(ethylthio)pyrimidine-4-amine

HRID 2171473

Reaction equation

HRID 2171473 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[NH:5][C:4](=[S:16])[N:3]=1.I[CH2:18][CH3:19].C(=O)(O)[O-].[Na+].O>CS(C)=O>[Cl:15][C:9]1[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[C:6]1[N:5]=[C:4]([S:16][CH2:18][CH3:19])[N:3]=[C:2]([NH2:1])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 583059934-Amino-6-(2,4-dichlorophenyl)pyrimidine-2(1H)-thione

Product 1

HCID 583060056-(2,4-Dichlorophenyl)-2-(ethylthio)pyrimidine-4-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

67.5 g (248 mmol) of 4-amino-6-(2,4-dichlorophenyl)pyrimidine-2(1H)-thione and 77.37 g (496.04 mmol) of iodoethane are dissolved in 560 ml of dry DMSO and, at RT, 270 ml of a saturated aqueous sodium bicarbonate solution are slowly added. The mixture is stirred at RT for 5 h and then 440 ml of water are added. The precipitate is filtered off with suction, washed with water and sucked dry. It is stirred twice with 100 ml of isopropanol each time and again filtered off with suction. It is washed once more with petroleum ether and the residue is dried under high vacuum. 50.0 g (67% of theory) of the product are obtained as a solid.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. washwashed with water
  3. customsucked dry
  4. stirringIt is stirred twice with 100 ml of isopropanol each time
  5. filtrationagain filtered off with suction
  6. washIt is washed once more with petroleum ether
  7. customthe residue is dried under high vacuum
  8. custom50.0 g (67% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-00ccfb01c6544563b70b06cf24c6caf1
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Linked notes

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