4-Methoxybenzyl alcohol → HCID 86756060, compound

HRID 1858328Notes

Reaction equation

HRID 1858328 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.Cl[C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[S:21])=[CH:18][N:17]=[C:16]([CH3:25])[N:15]=1>O1CCCC1>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:10][C:18]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[S:21])=[CH:14][N:15]=[C:16]([CH3:25])[N:17]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86756060HCID 86756060, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An ice-cooled suspension of 2.1 g (53 mmol) of sodium hydride (60% w/w dispersion in mineral oil) in 120 ml of tetrahydrofuran was treated dropwise with a solution of 6.5 g (47 mmol) of 4-methoxybenzyl alcohol in 40 ml of tetrahydrofuran. After 30 minutes, a solution of 10 g (43 mmol) of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate was added slowly. After a further 40 minutes the reaction was quenched by the cautious addition of 60 ml of saturated aqueous ammonium chloride. The mixture was separated and the organic phase dried over magnesium sulfate, filtered and evaporated to give 14.2 g (99%) of ethyl 4-(4-methoxy-benzyloxy)-2-methylthiopyrimidine-5-carboxylate as a pale yellow oil. [Mass spectrum (ESI) MH+ =335].

Workup

  1. customAfter a further 40 minutes the reaction was quenched by the cautious addition of 60 ml of saturated aqueous ammonium chloride
  2. customThe mixture was separated
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f271d8f1d4f24e19917c30c688da7fd9
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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