Morpholine → 4-(7-Bromo-2-chloroquinazolin-4-yl)morpholine

HRID 2092535

Reaction equation

HRID 2092535 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[N:7][C:8]([Cl:12])=[N:9]2)=[CH:4][CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:7][C:8]([Cl:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 341762487-Bromo-2,4-dichloroquinazoline

Product 1

HCID 866657584-(7-Bromo-2-chloroquinazolin-4-yl)morpholineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 7-bromo-2,4-dichloro-quinazoline (7 g, 0.0255 mol) in DCM (150 mL), morpholine (4.43 mL, 0.0509 mol) was slowly added and the reaction was continued at 0° C. for 30 min. The solvent was evaporated to dryness to get the crude compound. The crude product was purified, using column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to get the title compound (7 g, 84%). 1H NMR (300 MHz, CDCl3): δ 8.17 (d, J=7.5 Hz, 1H), 8.04 (d, J=7.5 Hz, 1H), 7.63 (d, J=8.1 Hz, 1H), 3.72-3.74 (m, 8H): LC-MS (ESI): Calculated mass: 327.0; Observed mass: 329.8 [M+H]+ (RT: 0.45 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-d929117b45b447578b1a411f9d617199
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Linked notes

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