Bromine → [2-(Bromoethyl)-6-(3-methoxyphenyl)pyrimidin-4-yl]-3-pyridylamine

HRID 30445Notes

Reaction equation

HRID 30445 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[N:4]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:29]Br>C(O)(=O)C>[Br:29][CH2:2][CH2:1][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[N:4]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 59789711[2-Ethyl-6-(3-methoxyphenyl)pyrimidin-4-yl]-3-pyridylamine

Product 1

HCID 86594232[2-(Bromoethyl)-6-(3-methoxyphenyl)pyrimidin-4-yl]-3-pyridylamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

[2-ethyl-6-(3-methoxyphenyl)pyrimidin-4-yl]-3-pyridylamine 14 (synthesized with a procedure similar to the one previously described) (1 eq) is dissolved in acetic acid, then sodium acetate (2 eq) is added. To this mixture, a solution of bromine (1 eq) in acetic acid is added dropwise. The reaction is stirred at room temperature for 3 h. The reaction mixture is concentrated under reduced pressure, water is added and the solution basified (pH ˜10-11) with sat. aq. Na2CO3 solution. The product 15 crashes out, is filtered off, dried, and used as is in the following step.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, water
  2. additionis added
  3. filtrationThe product 15 crashes out, is filtered off
  4. customdried

Sources & evidence

ORD record
ord-8041afd55de144adb16b24e7672d0245
Source dataset
uspto-grants-2008_09
Patent number
US07423148B2

Reaction notes

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