Water → HCID 59312819, compound

HRID 1529434Notes

Reaction equation

HRID 1529434 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 the mixture and the resulting suspension was filtered. The solid was dried and triturated with Hexanes to give 4-Chloro-6-(4-methoxy-benzyloxy)-2-methylsulfanyl-pyrimidine (75 g, 66.4% yield) as a white solid. MS (ESI, pos. ion) m/z: 297.0 (M+1); 1H NMR (400 MHz, CDCl3): δ 7.30-7.37 (m, 3H), 6.89-6.93 (m, 2H), 5.36 (s, 2H), 3.82 (s, 3H), 2.57 (s, 3H).

Workup

  1. temperaturecooled to RT
  2. filtrationthe resulting suspension was filtered
  3. customThe solid was dried
  4. customtriturated with Hexanes

Sources & evidence

ORD record
ord-e303bf18e5a249e292203228f471f3a4
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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