Morpholine → 2-Chloro-4-morpholino-6-fluoro-7-bromo-quinazoline

HRID 517450Notes

Reaction equation

HRID 517450 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][C:3]=1[F:14].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:7][C:8]([Cl:12])=[N:9]2)=[CH:4][C:3]=1[F:14]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 866657637-Bromo-2,4-dichloro-6-fluoroquinazoline

Product 1

HCID 866657622-Chloro-4-morpholino-6-fluoro-7-bromo-quinazolineYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 7-bromo-2,4-dichloro-6-fluoro-quinazoline (0.35 g, 0.001178 mol) in DCM (15 mL), morpholine (0.247 mL, 2.946 mol) was slowly added and the reaction was continued for 20 min. The reaction mixture was diluted with DCM and washed with water. The organic layer was dried over sodium sulfate and evaporated to get the crude. The crude was purified using column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to get the title compound (220 mg, 57%). 1H NMR (300 MHz, DMSO-d6): δ 8.16 (d, J=6.6 Hz, 1H), 8.01 (d, J=9.6 Hz, 1H), 3.83-3.86 (m, 4H), 3.76-3.73 (m, 4H); LC-MS (ESI): Calculated mass: 344.9; Observed mass: 347.8 [M+H]+ (RT: 1.70 min).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated
  4. customto get the crude
  5. customThe crude was purified

Sources & evidence

ORD record
ord-5ef9f59cdf1d433b9a7bcf5255fbc2c6
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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