Dichloromethane → 4-(5-Bromo-4-methylpyrimidin-2-yl)morpholine

HRID 2171670Notes

Reaction equation

HRID 2171670 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:3]=1.ClCCl.[Br:17]N1C(=O)CCC1=O>CCCCCC>[Br:17][C:7]1[C:2]([CH3:1])=[N:3][C:4]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 587422404-(4-Methylpyrimidin-2-yl)morpholine

Product 1

HCID 683089314-(5-Bromo-4-methylpyrimidin-2-yl)morpholineYield 86.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4-(4-Methylpyrimidin-2-yl)morpholine (300 mg) was mixed with dichloromethane (4 ml), and N-bromosuccinimide (357 mg) was added thereto at 0° C., followed by stirring at room temperature for 1 hour. Hexane was added to the reaction mixture, followed by purification by silica gel column chromatography (EtOAc/hexane), to obtain 4-(5-bromo-4-methylpyrimidin-2-yl) morpholine (372 mg).

Workup

  1. additionwas added
  2. customat 0° C.
  3. customfollowed by purification by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-11b804a9bd914456842acf3b6620a065
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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