Methanol → HCID 178490744, compound

HRID 1736391Notes

Reaction equation

HRID 1736391 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[O:4][CH:5]([C:10](OC)=[O:11])[C:6](OC)=[O:7].[NH2:20][C:21]([NH2:23])=[S:22].[CH3:24]O>>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[O:4][C:5]1[C:10]([OH:11])=[N:20][C:21]([S:22][CH3:24])=[N:23][C:6]=1[OH:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 2723790ThioureaHCID 21803835Dimethyl (2-chloro-5-methoxy-phenoxy)malonate

Product 1

HCID 178490744HCID 178490744, compound

Procedure

A solution of 230 mg of Na methylate in 15 ml of methanol, 1.45 g of dimethyl (2-chloro-5-methoxy-phenoxy)-malonate and 381 mg of thiourea was held at reflux for 5 hours. Then, the solvent was distilled off and the residue was dissolved in 10 ml of H2O. 630 mg of dimethyl sulfate were added to this solution and it was stirred at room temperature for 2 hours. 300 mg of acetic acid were then added, whereby the 5-(2-chloro-5-methoxy-phenoxy)-4,6-dihydroxy-2-methylsulfanyl-pyrimidine which formed separated. MS: 314 (M).

Workup

  1. temperatureat reflux for 5 hours
  2. distillationThen, the solvent was distilled off
  3. dissolutionthe residue was dissolved in 10 ml of H2O
  4. addition630 mg of dimethyl sulfate were added to this solution and it
  5. addition300 mg of acetic acid were then added

Sources & evidence

ORD record
ord-b0eceb52fe314ce4945e0d97dfccbb45
Source dataset
uspto-grants-1996_07
Patent number
US05541186

Reaction notes

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