Triethylamine → HCID 136037989, compound

HRID 1498771Notes

Reaction equation

HRID 1498771 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-7ca3c9cff29e41c5ba9029f16d500191
Source dataset
uspto-grants-2015_12
Patent number
US09199990B2

Reaction notes

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