Triethylamine → N-{[3-(Aminomethyl)oxetan-3-yl]methyl}-2-chloro-6-methylquinazolin-4-amine

HRID 540196Notes

Reaction equation

HRID 540196 reaction equation
[O:1]1[CH2:4][C:3]([CH2:7][NH2:8])([CH2:5][NH2:6])[CH2:2]1.C(N(CC)CC)C.[Cl:16][C:17]1[N:26]=[C:25](Cl)[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:28])[CH:23]=2)[N:18]=1>ClCCl.O>[NH2:6][CH2:5][C:3]1([CH2:7][NH:8][C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:28])[CH:23]=3)[N:18]=[C:17]([Cl:16])[N:26]=2)[CH2:4][O:1][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10953471[3-(Aminomethyl)oxetan-3-yl]methanamineHCID 142564832,4-Dichloro-6-methylquinazoline

Product 1

HCID 86691403N-{[3-(Aminomethyl)oxetan-3-yl]methyl}-2-chloro-6-methylquinazolin-4-amineYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of oxetane-3,3-diyldimethanamine (1.16 g, 10.0 mmol) and triethylamine (1.4 mL, 10 mol) in dichloromethane (15 mL) was added dropwise of a solution of 2,4-dichloro-6-methylquinazoline (500 mg, 2.36 mmol) in dichloromethane (5 mL). After being stirred at room temperature overnight, the resulting mixture was diluted with water (50 mL), and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 10% methanol in dichloromethane) to afford 300 mg of the desired product as a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (eluting with 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4d6b2aa585b14f4fb9c507a8367b85d1
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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