Ammonium Chloride → HCID 68227170, compound

HRID 1186494Notes

Reaction equation

HRID 1186494 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([N-]C(C)C)(C)C.[Li+].[CH3:32][S:33][C:34]1[N:39]=[C:38]([CH:40]=O)[CH:37]=[CH:36][N:35]=1.[Cl-].[NH4+]>C1COCC1>[CH3:2][O:3][CH:4]=[CH:40][C:38]1[CH:37]=[CH:36][N:35]=[C:34]([S:33][CH3:32])[N:39]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2724682Lithium diisopropylamideHCID 154070082-Methylsulfanylpyrimidine-4-carbaldehyde

Product 1

HCID 68227170HCID 68227170, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(Methoxymethyl)triphenylphosphonium chloride (68.6 g, 0.2 mol) was dissolved in THF (1000 mL), and lithium diisopropylamide (100 mL, 0.2 mol) was added to the solution at −20° C. After stirring at room temperature for 0.5 hour, the solution of 2-(methylthio)pyrimidine-4-carbaldehyde (15.4 g, 0.1 mol) in THF (400 mL) was added to the solution dropwise. The reaction mixture was stirred at room temperature overnight. Then saturated aqueous ammonium chloride solution (200 mL) was added to the mixture, extracted with ethyl acetate (1500 mL), and dried over with anhydrous sodium sulfate. The organic layer was concentrated and purified by chromatography (petroleum ether:ethyl acetate, 3:1) to give 4-(2-methoxy-vinyl)-2-methylsulfanyl-pyrimidine as a yellow solid. (Yield 11.2 g, 61.2%). LC-MS: [M+H]+ 183.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate (1500 mL)
  3. dry with materialdried over with anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated
  5. custompurified by chromatography (petroleum ether:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-29efd18646fd4fe3971b63139c416ada
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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