Dimethylacetamide → HCID 22180780, compound

HRID 1796112Notes

Reaction equation

HRID 1796112 reaction equation
C([Mg]Cl)(C)C.I[C:7]1[N:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][N:8]=1.[CH3:15][C:16](N(C)C)=[O:17]>C1COCC1>[CH3:14][O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:16](=[O:17])[CH3:15])[N:12]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 118066222-iodo-4-methoxypyrimidineHCID 178418918HCID 178418918, compound

Product 1

HCID 22180780HCID 22180780, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of isopropylmagnesium chloride (4.2 mmol) in THF (2.0M, 2.1 ml) was added dropwise to a stirred solution of 2-iodo-4-methoxypyrimidine (prepared according to Leprete et al. in Tetrahedron, 2000, 56, 265-273) (1.0 g, 4.2 mmol) in THF (12 ml) at 0° C. under N2. The reaction was stirred for 30 min at 0° C. and then DMA (409 μl, 4.4 mmol) was added. The reaction was stirred for 1 h and then quenched by addition of NH4Cl solution (15 ml) and extracted with EtOAc (50 ml and 20 ml). The combined organics were concentrated under reduced pressure and purified by column chromatography on silica, using 75% Et2O/iso-hexanes as eluent, to yield 1-(4-methoxypyrimidin-2-yl)ethanone (206 mg, 32%): 1H NMR (360 MHz, CDCl3) δ 8.59 (1H, d, J 5.7), 6.83 (1H, d, J 5.7), 4.08 (3H, s), 2.74 (3H, s); m/z (ES+) 153 (M+).

Workup

  1. stirringThe reaction was stirred for 1 h
  2. customquenched by addition of NH4Cl solution (15 ml)
  3. extractionextracted with EtOAc (50 ml and 20 ml)
  4. concentrationThe combined organics were concentrated under reduced pressure
  5. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-fe53bd4ae8dc438e839bc5f8e6d3948f
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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