Carbon Dioxide → 1-(2-Phenylpyrimidin-5-yl)ethanone

HRID 2274480Notes

Reaction equation

HRID 2274480 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5].[C:19](=O)=O.C[Mg]Cl.[Cl-].[NH4+]>C1COCC1.C(OCC)C.C(O)C>[C:12]1([C:9]2[N:10]=[CH:11][C:6]([C:4](=[O:5])[CH3:19])=[CH:7][N:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 47401292N-methoxy-N-methyl-2-phenylpyrimidine-5-carboxamideHCID 178418332HCID 178418332, compound

Product 1

HCID 226310721-(2-Phenylpyrimidin-5-yl)ethanoneYield 78%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution consisting of N-methoxy-N-methyl-2-phenylpyrimidine-5-carboxamide (Step I, 1.80 g, 7.39 mmol) in anhydrous THF (20 mL) was cooled in a −60° C. bath (ethanol, CO2(s)). Methylmagnesium chloride (Aldrich, 3.0 M in THF, 2.75 mL, 8.14 mmol) was subsequently added dropwise to the reaction mixture. The reaction mixture was stirred for 30 minutes in the −60+ C. bath and was subsequently allowed to warm to room temperature over one hour. The crude reaction mixture was then poured into a separatory funnel that contained diethyl ether (200 mL) and saturated ammonium chloride (150 mL). The organic layer was separated and the aqueous layer was washed again with diethyl ether (100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford a white solid as the crude product. The crude solid was triturated with a hexane-ethyl acetate (9:1 v/v) mixture (20 mL). The precipitate in solution was filtered to afford the title compound as a white solid (1.15 g, 78% yield); Rf 0.72 with 1:1 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) δ 9.25 (s, 2H), 8.53 (dd, 2H), 7.58 (m, 3H), 2.63 (s, 3H); MS (APCI+) m/z 199.0 (M+1).

Workup

  1. custombath and was subsequently allowed
  2. customThe crude reaction mixture
  3. additionwas then poured into a separatory funnel that
  4. customThe organic layer was separated
  5. washthe aqueous layer was washed again with diethyl ether (100 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford a white solid as the crude product
  10. customThe crude solid was triturated with a hexane-ethyl acetate (9:1 v/v) mixture (20 mL)
  11. filtrationThe precipitate in solution was filtered

Sources & evidence

ORD record
ord-e585928fa2054a88aa4d2439769cfcbd
Source dataset
uspto-grants-2015_09
Patent number
US09126973B2

Reaction notes

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