Bromine → HCID 68110300, compound

HRID 525078Notes

Reaction equation

HRID 525078 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, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Into a 250-mL round-bottom flask, was placed a solution of 4-N-[6-ethylthieno[2,3-d]pyrimidin-4-yl]-1-N,1-N-dimethylcyclohexane-1,4-diamine (4.0 g, 13.14 mmol, 1.00 equiv) in AcOH (40 mL), dibromane (4.2 g, 26.28 mmol, 2.00 equiv). The resulting solution was stirred overnight at 70° C. The resulting mixture was concentrated under vacuum. The residue was diluted with 50 mL of water. The pH value of the solution was adjusted to 8.0 with saturated sodium carbonate. The resulting solution was extracted with 4×50 mL of chloroform and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 3.0 g (60%) of 4-N-[5-bromo-6-ethylthieno[2,3-d]pyrimidin-4-yl]-1-N,1-N-dimethylcyclohexane-1,4-diamine as a yellow solid. MS (ES, m/z): 383 [M+H]+ 1H-NMR (400 MHz, DMSO-d6, ppm): δ 8.36 (1H, s), 6.75-6.77 (1H, d), 4.01-4.07 (1H, m), 2.81-2.88 (2H, q), 2.27 (7H, s), 2.09-2.11 (2H, d), 1.86 (2H, d), 1.32-1.40 (4H, q),1.21-1.26 (3H, t).

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe residue was diluted with 50 mL of water
  4. extractionThe resulting solution was extracted with 4×50 mL of chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThis resulted in 3.0 g (60%) of 4-N-[5-bromo-6-ethylthieno[2,3-d]pyrimidin-4-yl]-1-N,1-N-dimethylcyclohexane-1,4-diamine as a yellow solid

Sources & evidence

ORD record
ord-9ee69f46a0c14878be081a7c30265cfd
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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