N-bromobutanimide → 2-Bromo-1-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)ethanone

HRID 2036827Notes

Reaction equation

HRID 2036827 reaction equation
[Br:1]N1C(=O)CCC1=O.O1CCOCC1.O.C([O:18][C:19]([C:21]1[N:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:22]=1)=[CH2:20])C>O>[Br:1][CH2:18][C:19]([C:21]1[N:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:22]=1)=[O:20]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 218864351,4-Dioxane--water (1/1)HCID 670559512-(1-ethoxyvinyl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine

Product 1

HCID 866706182-Bromo-1-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)ethanoneYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-bromosuccinimide (0.55 g, 3.1 mmol) was added to 1,4-dioxane/water (3:1) (20 mL). 2-(1-Ethoxyvinyl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine (0.59 g, 1.5 mmol) was then added in small portions at 0° C. Upon completion of addition, the reaction mixture was stirred at room temperature for 20 min. After this time, water was added and the aqueous portion was extracted twice with DCM. The combined organic layers were dried, filtered and evaporated under reduced pressure to yield 2-bromo-1-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)ethanone (600 mg, 69% purity by LCMS), which was used without further purification. LCMS Method Y: retention time 1.996 min, [M+1]=433.

Workup

  1. additionUpon completion of addition
  2. extractionthe aqueous portion was extracted twice with DCM
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-111740ebbe794142be513d71a6be5f4b
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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