Sodium Chloride → 5-(benzyloxy)-2-(hydroxymethyl)-3-methyl-4(3H)-pyrimidinone

HRID 1755869Notes

Reaction equation

HRID 1755869 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]=[C:12]([CH2:15][OH:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[Na+].[Na+].CI.[Cl-].[Na+]>CO.ClCCl>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]([CH3:18])[C:12]([CH2:15][OH:16])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 178517848HCID 178517848, compound

Product 1

HCID 199178305-(benzyloxy)-2-(hydroxymethyl)-3-methyl-4(3H)-pyrimidinoneYield 49.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(Benzyloxy)-2-(hydroxymethyl)-4(1H)-pyrimidinone (2.3 g) are dissolved in 20 ml of absolute methanol. The solution is treated with 4.24 g (40 mmol) of sodium carbonate and 10 ml of methyl iodide and stirred at room temperature for 4 days. Now, 400 ml of dichloromethane and 100 ml of saturated sodium chloride solution are added thereto, the organic phase is separated, dried over sodium sulphate and concentrated. The residue is chromatographed of 100 g of silica gel (0.063-0.2 mm). The two products are eluted in succession with dichloromethane/methanol (9:1 v/v). There are obtained 1.2 g of 5-(benzyloxy)-2-(hydroxymethyl)-3-methyl-4(3H)-pyrimidinone as white crystals from ether, m.p. 83°-84° C. 5-(Benzyloxy)-2-(hydroxymethyl)-1-methyl-4(1H)-pyrimidinone also forms white crystals from ether, m.p. 172°-173° C. 0.6 g is obtained.

Workup

  1. customthe organic phase is separated
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. customThe residue is chromatographed of 100 g of silica gel (0.063-0.2 mm)
  5. washThe two products are eluted in succession with dichloromethane/methanol (9:1 v/v)

Sources & evidence

ORD record
ord-c6116454f18c4fb4b4a1cb7376284549
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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