Triethylamine → HCID 15953858, compound

HRID 1714851Notes

Reaction equation

HRID 1714851 reaction equation
[I:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31]>O1CCCC1>[NH2:15][C:9]1[C:8]([O:7][C:6]2[CH:16]=[C:2]([I:1])[C:3]([O:20][CH3:21])=[CH:4][C:5]=2[CH:17]([CH3:19])[CH3:18])=[CH:13][N:12]=[C:11]([NH:14][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 159538025-(5-Iodo-2-isopropyl-4-methoxyphenoxy)pyrimidine-2,4-diamine

Product 1

HCID 15953858HCID 15953858, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (1 g, 2.50 mmol), dissolved in anhydrous tetrahydrofuran, was added triethylamine (0.38 mL, 2.75 mmol) and isobutyryl chloride (0.29 mL, 2.75 mmol). After stirring 30 minutes, the reaction was concentrated under reduced pressure. The residue was dissolved in dichloromethane (100 mL), and the dichloromethane layer was washed with water, dried using anhydrous sodium sulfate, and concentrated under reduced pressure. Purification by silica gel column chromatography eluting with 96/4/0.1 dichloromethane/methanol/ammonium hydroxide yielded 634 mg (54%) of N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-isobutyramide as pale yellow solid, MS (M+H)=471.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  3. washthe dichloromethane layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography
  7. washeluting with 96/4/0.1 dichloromethane/methanol/ammonium hydroxide

Sources & evidence

ORD record
ord-a176b96cde694476948e77f1272ad29f
Source dataset
uspto-grants-2010_09
Patent number
US07799796B2

Reaction notes

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