Potassium Iodide → 3-(4-Methoxybenzyl)-6-(methylamino)pyrimidin-4(3H)-one

HRID 1260429Notes

Reaction equation

HRID 1260429 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][NH:6][C:5](=[O:9])[CH:4]=1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:6]2[C:5](=[O:9])[CH:4]=[C:3]([NH:2][CH3:1])[N:8]=[CH:7]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 1354814476-(Methylamino)pyrimidin-4-ol

Product 1

HCID 598230433-(4-Methoxybenzyl)-6-(methylamino)pyrimidin-4(3H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methylamino)pyrimidin-4(3H)-one (100 g, 800 mmol, 1 eq), p-methoxybenzyl chloride (124.8 g, 800 mmol, 1 eq), potassium iodide (13.3 g, 80 mmol, 0.1 eq) and cesium carbonate (260 g, 800 mmol, 1 eq) were stirred at RT in anhydrous DMF (1 L) for 8 hours. The DMF was removed in vacuo and the residue stirred overnight in 20% methanol/DCM. The solid was removed by filtration and washed with 20% methanol/DCM. The solvent was removed in vacuo and the resulting residue taken up in DCM then washed with water. The organic layer was dried over magnesium sulfate and evaporated to give 102 g of the title compound (59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.63 (d, J=4.29 Hz, 3H) 3.72 (s, 3H) 4.87 (s, 2H) 6.88 (d, J=8.84 Hz, 2H) 7.25 (d, J=8.59 Hz, 2H) 8.22 (s, 1H). [M+H] calc'd for C13H15N3O2, 246. found, 246.

Workup

  1. customThe DMF was removed in vacuo
  2. customThe solid was removed by filtration
  3. washwashed with 20% methanol/DCM
  4. customThe solvent was removed in vacuo
  5. washthen washed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-fafbc4459afe423ba01ee8a64d37bebf
Source dataset
uspto-grants-2013_06
Patent number
US08470837B2

Reaction notes

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