Potassium Carbonate → 4-Chloro-6-(6-methylsulfanyl-pyridin-3-ylamino)-pyrimidine-5-carbonitrile

HRID 1036754Notes

Reaction equation

HRID 1036754 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[Cl:10][C:11]1[C:16]([C:17]#[N:18])=[C:15](Cl)[N:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:10][C:11]1[C:16]([C:17]#[N:18])=[C:15]([NH:9][C:6]2[CH:7]=[N:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)[N:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5993714,6-Dichloropyrimidine-5-carbonitrileHCID 102611796-(Methylsulfanyl)pyridin-3-amine

Product 1

HCID 859846374-Chloro-6-(6-methylsulfanyl-pyridin-3-ylamino)-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methylsulfanyl-pyridin-3-ylamine (500.0 mg, 3.57 mmol, 1.0 equivalent) in DMF (1 mL) was added drop wise to a suspension of 4,6-dichloro-pyrimidine-5-carbonitrile (616.9 mg, 3.57 mmol, 1.0 equivalent), potassium carbonate (542.1 mg, 3.92 mmol, 1.1 equivalent) at 0° C. under stirring. The reaction was left reacting at room temperature for 1.5 hours. Product was crystallized using ethyl acetate, hexane getting a yellow solid as product (650.00 mg, 65.62%). LCMS (ESI) for C11H8ClN5S: m/z 278.0 (M+H+, 100%).

Workup

  1. waitThe reaction was left
  2. customProduct was crystallized

Sources & evidence

ORD record
ord-0dc927e69a684ae9abd71429f51d8457
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

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