5-Isopropyl-6-chloro-2,4-dimethoxypyrimidine → 6-Chloro-5-isopropylpyrimidine-2,4(1H,3H)-dione

HRID 2194760Notes

Reaction equation

HRID 2194760 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11]C)[N:5]=[C:4]([O:13]C)[N:3]=1>Cl.CO>[Cl:1][C:2]1[NH:3][C:4](=[O:13])[NH:5][C:6](=[O:11])[C:7]=1[CH:8]([CH3:10])[CH3:9]

Participants

3

Reactant 1

HCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidine

Product 1

HCID 111270436-Chloro-5-isopropylpyrimidine-2,4(1H,3H)-dioneYield 700.4%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

4-Chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (40 g, 18.47 mmol) was dissolved in 150 mL of conc. HCl-methanol (1:2) and refluxed for 6 hr. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, chloroform:methanol (from 95:5 to 90:10)) to give 24.4 g (70%) of 6-chloro-5-isopropyl-1H-pyrimidine-2,4-dione as a white solid. m.p. 250-251° C.; 1H-NMR (200 MHz, CDCl3) δ 1.25 (6H, d, J=7.1 Hz), 3.13 (1H, m); m/z (EI) 188 (M+).

Workup

  1. temperaturerefluxed for 6 hr
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, chloroform:methanol (from 95:5 to 90:10))

Sources & evidence

ORD record
ord-4d850f2857454f53b282d14fbcef761a
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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