Morpholine → 4-(8-Bromo-2-chloroquinazolin-4-yl)morpholine

HRID 517455Notes

Reaction equation

HRID 517455 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[C:7]2Cl.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[C:7]2[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 137858748-Bromo-2,4-dichloroquinazoline

Product 1

HCID 866657654-(8-Bromo-2-chloroquinazolin-4-yl)morpholineYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 8-bromo-2,4-dichloro-quinazoline (5.5 g, 0.0197 mol) in DCM (100 mL), morpholine (3.77 mL, 0.0433 mol) was slowly added and the reaction was continued for 15 min. The solvent was evaporated to dryness to get the crude compound. The crude product was purified, using column chromatography (60-120 silica gel, 5-30% ethyl acetate in hexane) to get the title compound [2.5 g, 39%]. 1H NMR (400 MHz, CDCl3): δ 8.05 (dd, J′=7.8 Hz, J″=1.2 Hz, 1H), 7.81 (dd, J′=8.4 Hz, J″=0.9 Hz, 1H), 7.29 (t, J=8.4 Hz, 1H), 3.89 (s, 8H); LC-MS (ESI): Calculated mass: 326.9; Observed mass: 327.9 [M+H]+ (RT: 1.57 min).

Workup

  1. customThe solvent was evaporated to dryness
  2. customto get the crude compound
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-92fcd1f41333419690b6139e89bd0431
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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