Water → HCID 59312819, compound

HRID 634323Notes

Reaction equation

HRID 634323 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:20][CH2:19][C:16]2[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=2)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 11430Potassium CarbonateHCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Product 1

HCID 59312819HCID 59312819, compoundYield 658.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4,6-dichloro-2-(methyl thio)pyrimidine (75 g, 38.4 mmol, Sigma-Aldrich) in DMF (750 mL) was added p-methoxybenzyl alcohol (58.38 g, 42.1 mmol) and K2CO3 (212.3 g, 1538 mmol). The reaction was stirred at 60° C. for 12 h, then cooled to RT. Water (500 mL) was added to get a white solid and the mixture was filtered. The resulting solid was triturated with hexanes to give 4-chloro-6-((4-methoxybenzyl)oxy)-2-(methylthio)pyrimidine (75 g, 66.4%) as white solid. MS (ESI, pos. ion) m/z: 297 (M+1).

Workup

  1. temperaturecooled to RT
  2. customto get a white solid
  3. filtrationthe mixture was filtered
  4. customThe resulting solid was triturated with hexanes

Sources & evidence

ORD record
ord-b766cfe5cebc4e53be83ffd0521d4305
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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