Potassium Iodide → HCID 86650746, compound

HRID 875210Notes

Reaction equation

HRID 875210 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=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>[CH3:15][N:14]1[C:10]([C:3](=[N:2][O:1][CH2:17][C:18]2[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:11][N:12]=[CH:13]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 212988272-(Chloromethyl)pyrimidin-4-amineHCID 86650744HCID 86650744, compound

Product 1

HCID 86650746HCID 86650746, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-phenylmethanimine (3.90 g, 19.4 mmol) and 2-(chloromethyl)pyrimidin-4-amine (3.06 g, 21.3 mmol) in acetonitrile (50 mL) were added cesium carbonate (13.3 g, 40.7 mmol) and potassium iodide (322 mg, 1.93 mmol). After stirring at room temperature for 29 h, N-N-dimethylformamide (5 mL) was added and the mixture was further at room temperature for 72 h. The reaction mixture was filtered, the insolubles washed with acetone, and the filtrate concentrated in vacuo. Purification on silica gel afforded 2-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-amine [3.61 g, yield 16%; HPLC/MS: m/z=309 (M+H); log P(HCOOH)<0.23].

Workup

  1. waitthe mixture was further at room temperature for 72 h
  2. filtrationThe reaction mixture was filtered
  3. washthe insolubles washed with acetone
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-b7330a361eab421385c515cf413b3ad4
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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