Triethylamine → HCID 136037989, compound

HRID 336786Notes

Reaction equation

HRID 336786 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[NH:21][C:20](=[O:22])[C:19]3[C:14](=[CH:15][C:16]([O:25][CH3:26])=[CH:17][C:18]=3[O:23][CH3:24])[N:13]=2)=[CH:7][C:6]=1[CH3:27].[CH3:28][N:29]=[C:30]=[O:31].CCN(CC)CC>C1COCC1>[CH3:24][O:23][C:18]1[CH:17]=[C:16]([O:25][CH3:26])[CH:15]=[C:14]2[C:19]=1[C:20](=[O:22])[NH:21][C:12]([C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([O:4][CH2:3][CH2:2][NH:1][C:30]([NH:29][CH3:28])=[O:31])=[C:6]([CH3:27])[CH:7]=1)=[N:13]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 136037976HCID 136037976, compound

Product 1

HCID 136037989HCID 136037989, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound 2-(4-(2-aminoethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.10 g, 0.27 mmol), methylisocyanate (0.020 g, 0.35 mmol), and Et3N (0.034 g, 0.35 mmol) in THF (4.0 mL) was stirred at room temperature for 16 hours. The mixture was filtered, washed with CH2Cl2 and the solvent was removed under reduced pressure. The resulting residue was chromatographed on silica gel to yield the title compound (0.082 g, 71%) as a white solid: MS (APCI) m/z 449 [M+Na]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with CH2Cl2
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-9da7af60fe184887b3c3b9bc41e75a70
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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