1-Iodopropane → HCID 66955592, compound

HRID 1399566Notes

Reaction equation

HRID 1399566 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[N:8]=[C:7]([CH3:9])[C:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:33][CH2:34][CH3:35]>CN(C=O)C>[CH3:21][N:2]([CH3:1])[C:3]1[N:8]=[C:7]([CH3:9])[C:6]([CH:10]([CH2:33][CH2:34][CH3:35])[C:11]([O:13][CH3:14])=[O:12])=[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66955908HCID 66955908, compound

Product 1

HCID 66955592HCID 66955592, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of methyl 2-(2-(dimethylamino)-4-methyl-6-phenylpyrimidin-5-yl)acetate (750 mg; 2.63 mmol) in dry DMF (13 mL) was cooled to −15° C. LHMDS (2.89 mL, 2.89 mmol; 1M in THF) was added dropwise and the mixture was stirred at −15° C. for 15 min followed by the dropwise addition of iodopropane (0.385 mL; 3.94 mmol), after stirring for 2 h at −15° C. the mixture was allowed to warm up to room temperature. After 1 h the reaction was quenched by adding a saturated solution of ammonium chloride. The mixture was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane to give 680 mg (79%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.46-7.40 (5H, m); 3.82 (1H, dd, J=6.1, 8.2 Hz); 3.69 (3H, s); 3.19 (6H, s); 2.31 (3H, s); 2.08-1.96 (1H, m); 1.62-1.47 (1H, m); 1.02-0.92 (2H, m); 0.65 (3H, t, J=7.1 Hz).

Workup

  1. stirringafter stirring for 2 h at −15° C. the mixture
  2. temperatureto warm up to room temperature
  3. customAfter 1 h the reaction was quenched
  4. additionby adding a saturated solution of ammonium chloride
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane

Sources & evidence

ORD record
ord-98e42b5535814c8f85c1921eccb00b9a
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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