Potassium Iodide → HCID 86650742, compound

HRID 875204Notes

Reaction equation

HRID 875204 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[N:11]([CH3:15])[CH:12]=[CH:13][N:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O.C(=O)(O)[O-].[Na+]>[CH3:15][N:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:3](=[N:2][O:1][CH2:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 212988272-(Chloromethyl)pyrimidin-4-amineHCID 136331255HCID 136331255, compound

Product 1

HCID 86650742HCID 86650742, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-2-yl)-1-phenylmethanimine (3.50 g, 17.4 mmol) and 2-(chloromethyl)pyrimidin-4-amine (2.62 g, 18.3 mmol) in acetonitrile (120 mL) were added cesium carbonate (5.67 g, 17.4 mmol) and potassium iodide (289 mg, 1.74 mmol). After stirring 6 h at 60° C., overnight at room temperature, then again 8 h at 60° C., the reaction mixture was diluted with water (150 mL), sat. aq. sodium bicarbonate (50 mL) and extracted with dichloromethane (2×100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford 2-[({[(1-methyl-1H-imidazol-2-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-amine as a foamy solid [4.80 g, yield 76%; HPLC/MS: m/z=309 (M+H); log P(Neutral)=1.42].

Workup

  1. extractionextracted with dichloromethane (2×100 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14d89c993715454d9f562ddb79220508
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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