Iodoethane → HCID 11259682, compound

HRID 969296Notes

Reaction equation

HRID 969296 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[NH:13][C:14]1[N:15]=[C:16]([CH3:29])[C:17]2[CH2:23][CH2:22][CH2:21][N:20]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:18]=2[N:19]=1.I[CH2:31][CH3:32]>CN(C)C=O>[Br:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:7]=[CH:6][C:5]=1[N:13]([CH2:31][CH3:32])[C:14]1[N:15]=[C:16]([CH3:29])[C:17]2[CH2:23][CH2:22][CH2:21][N:20]([CH:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[C:18]=2[N:19]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11419018HCID 11419018, compound

Product 1

HCID 11259682HCID 11259682, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a vigorously stirred suspension of sodium hydride (0.004 g, 0.17 mmol) in N,N-dimethylformamide (0.5 mL) under nitrogen was added a solution of (2-bromo-4-isopropyl-phenyl)-[8-(1-ethyl-propyl)-4-methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-2-yl]-amine (XIV; 0.056 g, 0.13 mmol) in N,N-dimethylformamide (0.5 mL). After 30 minutes at room temperature, iodoethane (0.026 g, 0.17 mmol) was added, and the resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was then poured onto water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were washed with brine (10 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The yellow oil so obtained was chromatographed over silica gel, eluting with a gradient of 20 to 50% ethyl acetate in hexane, to afford 116 as a pale yellow oil (0.040 g, 67%). ESIMS m/z 459 (M+H).

Workup

  1. additionThe reaction mixture was then poured onto water (20 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined extracts were washed with brine (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe yellow oil so obtained
  8. customwas chromatographed over silica gel
  9. washeluting with a gradient of 20 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-30e75ecda616448193dd72b5b3bd1dc5
Source dataset
uspto-grants-2007_12
Patent number
US07307082B2

Reaction notes

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