Triethylamine → N-[(3-Aminooxetan-3-yl)methyl]-2-chloroquinazolin-4-amine

HRID 540202Notes

Reaction equation

HRID 540202 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][CH2:14][C:15]1([NH2:19])[CH2:18][O:17][CH2:16]1.C(N(CC)CC)C>CO>[NH2:19][C:15]1([CH2:14][NH:13][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([Cl:1])[N:11]=2)[CH2:18][O:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2528862,4-DichloroquinazolineHCID 217130163-(Aminomethyl)oxetan-3-amine

Product 1

HCID 86691405N-[(3-Aminooxetan-3-yl)methyl]-2-chloroquinazolin-4-amineYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4-dichloroquinazoline (1.0 g, 5.024 mmol) in methanol (15 mL) was added 3-(aminomethyl)oxetan-3-amine (855 mg, 60%, 5.024 mmol) and triethylamine (101 mg, 1.005 mmol). After being stirred at room temperature overnight, the mixture was concentrated in vacuo. The residue was purified by flash column chromatography to afford 1.2 g of the desired product as a white solid (yield was 92%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ed5f1cc09e1e4dbab5a9729bda253ceb
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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