Methyl chloroformate → Methyl 2-(4,6-dimethoxypyrimidin-2-yl)-2-fluoro-2-phenylacetate

HRID 1440963Notes

Reaction equation

HRID 1440963 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([CH:23]([F:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:16]=1.Cl[C:32]([O:34][CH3:35])=[O:33].[Cl-].[NH4+]>O1CCCC1>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([O:14][CH3:13])[N:16]=[C:17]([C:23]([F:30])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:32]([O:34][CH3:35])=[O:33])[N:18]=1

Participants

7

Reactant 5

HCID 6586Methyl chloroformateHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 541012184,6-Dimethoxy-2-(alpha-fluorobenzyl) pyrimidineHCID 178418339Butyllithium

Product 1

HCID 22420764Methyl 2-(4,6-dimethoxypyrimidin-2-yl)-2-fluoro-2-phenylacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

n-Butyllithium (2.5M in hexane, 1.7 ml) was added to diisopropylamine (0.59 ml) under nitrogen in dry tetrahydrofuran (15 ml) at -78° C. This solution was stirred for 30 minutes, then a solution of the product of stage (a) above (1.0 g) in tetrahydrofuran (10 ml) was added over 20 minutes. Methyl chloroformate (0.4 g) in dry tetrahydrofuran (10 ml) was added over 15 minutes at -78° C., and the reaction mixture was allowed to warm slowly to room temperature, after which it was added to aqueous ammonium chloride solution. The mixture was extracted with ether, the extracts being washed with water, dried over magnesium sulfate, and evaporated to dryness to give 1.08 g of the desired product, identical to that of Method A above.

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe extracts being washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-1b7bd2fdfe634330967fe57bb3cd7801
Source dataset
uspto-grants-1996_03
Patent number
US05502028

Reaction notes

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