Water → HCID 67451926, compound

HRID 1852963Notes

Reaction equation

HRID 1852963 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[NH:5][C:4](=[S:15])[N:3]=1.I[CH2:17][CH3:18].C(=O)(O)[O-].[Na+].O>CS(C)=O>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[N:5]=[C:4]([S:15][CH2:17][CH3:18])[N:3]=[C:2]([NH2:1])[CH:7]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340Iodoethane2×HCID 516892Sodium BicarbonateHCID 82093952HCID 82093952, compound

Product 1

HCID 67451926HCID 67451926, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-amino-6-(4-bromophenyl)pyrimidine-2(1H)-thione (53.90 g, 191.0 mmol) and iodoethane (16.96 mL, 210.1 mmol) in 200 mL of DMSO was slowly added 200 mL of aqueous saturated sodium bicarbonate at ambient temperature with stirring. The reaction was allowed to stir for 1 hour before iodoethane (8.0 mL, 99.1 mmol) was added. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was poured into 500 mL of water and stirred for 20 minutes. The solid was collected by means of vacuum filtration and was dried under high vacuum overnight to afford 6-(4-bromophenyl)-2-(ethylthio)pyrimidin-4-amine (51.0 g, 156.2 mmol, 81.76% yield). MS (apci) m/z=310.0 (M+H).

Workup

  1. customat ambient temperature
  2. additionwas added
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. stirringstirred for 20 minutes
  5. filtrationThe solid was collected by means of vacuum filtration
  6. customwas dried under high vacuum overnight

Sources & evidence

ORD record
ord-e1d88dd8cd5e42e19e42d4f0770f3e49
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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