Water → HCID 59312819, compound

HRID 1429185Notes

Reaction equation

HRID 1429185 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([S:21][CH3:22])[N:15]=1.O>CN(C=O)C.C1COCC1>[Cl:13][C:14]1[CH:19]=[C:18]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:17]=[C:16]([S:21][CH3:22])[N:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Product 1

HCID 59312819HCID 59312819, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxybenzyl alcohol (8.9 g, 65 mmol) in dry DMF (100 ml) was added a 60% suspension of sodium hydride (2.2 g, 55 mmol) in portions and the mixture was stirred for two hours at room temperature. The mixture was cooled in an ice bath and 4,6-dichloro-2-methylsulfanyl-pyrimidine (9.8 g, 50 mmol) in dry THF (20 ml) was added. The mixture was then stirred for 72 h at room temperature. Water was added and the mixture was extracted twice with ethyl acetate. The organic phase was washed with water, dried with sodium sulphate and evaporated under reduce pressure. The residue was purified by silica gel chromatography eluted with hexane ethyl acetate which gave the title compound (9.1 g, 61%), (M+H)+296

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringThe mixture was then stirred for 72 h at room temperature
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried with sodium sulphate
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with hexane ethyl acetate which

Sources & evidence

ORD record
ord-a39708ffa9e147e095395b17e1f12033
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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