N-bromobutanimide → HCID 44409749, compound

HRID 1984318Notes

Reaction equation

HRID 1984318 reaction equation
[Br:1]N1C(=O)CCC1=O.[N:9]1([C:16]2[N:21]=[C:20]([CH:22]3[CH2:24][CH2:23]3)[N:19]=[C:18]([NH:25][CH:26]3[CH2:28][CH2:27]3)[CH:17]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C(Cl)(Cl)Cl.ClCCl>[N:9]1([C:16]2[N:21]=[C:20]([CH:22]3[CH2:24][CH2:23]3)[N:19]=[C:18]([NH:25][CH:26]3[CH2:28][CH2:27]3)[C:17]=2[Br:1])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 44409745HCID 44409745, compound

Product 1

HCID 44409749HCID 44409749, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

N-Bromosuccinimide (0.39 g, 2.2 mmol) is added to a solution of 6-(1-azepanyl)-N,2-dicyclopropyl-4-pyrimidinamine 62 (0.5 g, 1.84 mmol) in chloroform (2 ml). The mixture is stirred at 60° C. overnight then cooled, diluted with dichloromethane and washed two times with water. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo. The crude mixture is purified by column chromatography (dichloromethane/ethanol: 97/3) to give pure 6-azepan-1-yl-5-bromo-N,2-dicyclopropylpyrimidin-4-amine 61 (134 mg, 21%) as a brownish paste.

Workup

  1. temperaturethen cooled
  2. washwashed two times with water
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture is purified by column chromatography (dichloromethane/ethanol: 97/3)

Sources & evidence

ORD record
ord-014545d9319648f6b6e51067736f67c2
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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