Bromine → HCID 68110300, compound

HRID 525083Notes

Reaction equation

HRID 525083 reaction equation
[CH2:1]([C:3]1[S:21][C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH:11][CH:12]3[CH2:17][CH2:16][CH:15]([N:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)[C:5]=2[CH:4]=1)[CH3:2].[Br:22]Br>CC(O)=O>[Br:22][C:4]1[C:5]2[C:10]([NH:11][CH:12]3[CH2:17][CH2:16][CH:15]([N:18]([CH3:19])[CH3:20])[CH2:14][CH2:13]3)=[N:9][CH:8]=[N:7][C:6]=2[S:21][C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 68110511HCID 68110511, compound

Product 1

HCID 68110300HCID 68110300, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Into a 250-mL round-bottom flask containing a solution of 4-N-[6-ethylthieno[2,3-d]pyrimidin-4-yl]-1-N,1-N-dimethylcyclohexane-1,4-diamine (2 g, 6.57 mmol, 1.00 equiv) in AcOH (40 mL) was added Br2 (2.1 g, 13.14 mmol, 2.00 equiv) at room temperature. The resulting solution was stirred overnight at 70° C. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 9 with sodium carbonate (sat.) and extracted with 3×200 mL of ethyl acetate. The combined.organic layers were washed with 300 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give the resulted 4-N-[5-bromo-6-ethylthieno[2,3-d]pyrimidin-4-yl]-1-N,1-N-dimethylcyclohexane-1,4-diamine (0.9 g, crude) as a brown solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. extractionextracted with 3×200 mL of ethyl acetate
  3. washThe combined.organic layers were washed with 300 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-18f58a2b49234575b304a33a9c6b57c6
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

Loading…