Aluminium lithium hydride → (4-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidin-5-yl)methanol

HRID 431051Notes

Reaction equation

HRID 431051 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][S:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([Cl:25])[CH:18]=2)[C:12]([C:26](OCC)=[O:27])=[CH:11][N:10]=1>O1CCCC1>[CH3:7][S:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([Cl:25])[CH:18]=2)[C:12]([CH2:26][OH:27])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22025927Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 22025932(4-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidin-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (4.15 g) in tetrahydrofuran (150 ml) is added a solution of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (38.32 g) in tetrahydrofuran (100 ml) under ice-cooling at 5° C. to 10° C. over a period of one hour. After the addition, the ice bath is removed, and the reaction mixture is stirred at room temperature for one hour. To the reaction mixture is added water (4.15 ml) under ice-cooling, and thereto is further added 3N aqueous sodium hydroxide solution (4.15 ml). To the mixture is added water (4.15 ml) three times, and the mixture is stirred at room temperature for one hour. The reaction mixture is treated with magnesium sulfate, and the solid precipitates obtained are filtered. The precipitates are washed with tetrahydrofuran. The filtrate and the washings are combined, and concentrated under reduced pressure, and triturated with a mixture of ethyl acetate and isopropyl ether. The resulting crystals are collected by filtration, and washed well with isopropyl ether to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-hydroxymethylpyrimidine as pale yellow crystalline powder.

Workup

  1. temperaturecooling at 5° C. to 10° C. over a period of one hour
  2. additionAfter the addition
  3. customthe ice bath is removed
  4. additionTo the reaction mixture is added water (4.15 ml) under ice-
  5. temperaturecooling
  6. additionTo the mixture is added water (4.15 ml) three times
  7. stirringthe mixture is stirred at room temperature for one hour
  8. additionThe reaction mixture is treated with magnesium sulfate
  9. customthe solid precipitates
  10. customobtained
  11. filtrationare filtered
  12. washThe precipitates are washed with tetrahydrofuran
  13. concentrationconcentrated under reduced pressure
  14. customtriturated with a mixture of ethyl acetate and isopropyl ether
  15. filtrationThe resulting crystals are collected by filtration
  16. washwashed well with isopropyl ether

Sources & evidence

ORD record
ord-fb0a894f0e674369a2e681d5d0a8336a
Source dataset
uspto-grants-2003_12
Patent number
US06656935B2

Reaction notes

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