Potassium Carbonate → 5-Chloro-2-((pyrimidin-2-ylmethyl)thio)aniline

HRID 70385Notes

Reaction equation

HRID 70385 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].Cl[CH2:11][C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([S:9][CH2:11][C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:2]([CH:7]=1)[NH2:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120002-Amino-4-chlorobenzenethiolHCID 128773712-(Chloromethyl)pyrimidine

Product 1

HCID 626988105-Chloro-2-((pyrimidin-2-ylmethyl)thio)anilineYield 50.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following General Procedure A, the title compound (284 mg, 39%) was prepared from 2-amino-4-chlorobenzenethiol (529 mg, 3.33 mmol), 2-(chloromethyl)pyrimidine (366 mg, 2.22 mmol) and K2CO3 (1.53 g, 11.09 mmol) in DMF (10 ml).

Sources & evidence

ORD record
ord-ceb2e49da3494bfeabf6cf6912ffa254
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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