Cesium carbonate → HCID 18507357, compound

HRID 1356158Notes

Reaction equation

HRID 1356158 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Br)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][C:20]1[CH:24]=[CH:23][NH:22][N:21]=1>CN1C(=O)CCC1>[NH2:1][C:2]1[N:7]=[C:6]([N:22]2[CH:23]=[CH:24][C:20]([CH3:19])=[N:21]2)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrileHCID 178428694HCID 178428694, compound

Product 1

HCID 18507357HCID 18507357, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2.05 g (8.36 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 15 ml NMP were added 3.00 g (9.20 mmol) cesium carbonate and 0.74 ml (9.20 mmol) 3-methyl-pyrazole and the mixture heated at 70° C. for 16 h. The reaction mixture was then poured into 400 ml ice-water and the resulting precipitate collected by filtration. Chromatography (ethyl acetate/hexane 1/1 then 2/1) afforded 230 mg (11%) 2-amino-4-(3-methyl-pyrazol-1-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 247 (M+H+, 100).

Workup

  1. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-4fadded625854380962a1fab3b9eb5a3
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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