Bromine → HCID 178423301, compound

HRID 1371222Notes

Reaction equation

HRID 1371222 reaction equation
[ClH:1].[CH3:2][CH:3]1[CH2:8][CH:7]([C:9]2[NH:14][C:13]3=[CH:15][CH:16]=[N:17][C:12]3=[CH:11][N:10]=2)[CH2:6][CH:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:4]1.[Br:24]Br>CC(O)=O.O>[ClH:1].[Br:24][C:15]1[CH:16]=[N:17][C:12]2[C:13]=1[NH:14][C:9]([CH:7]1[CH2:6][CH:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:4][CH:3]([CH3:2])[CH2:8]1)=[N:10][CH:11]=2

Participants

5

Reactant 2

HCID 24408BromineHCID 178423311HCID 178423311, compound

Product 1

HCID 178423301HCID 178423301, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To an oven-dried, 50-mL, round-bottomed flask was added 2-methyl-6-phenyl-4-(piperidinyl)pyrrolo[3,2-d]pyrimidine (Example 35)) (500 mg, 1.71 mmol) which was dissolved in glacial AcOH (15 mL). To this solution was added Br2 (Aldrich Chemical Company) (90.0 mL, 1.8 mmol) dropwise over 2 min. The resulting dark mixture was diluted with H2O (10 mL) and the mixture was warmed to 45° C. and stirred for 2 h. The reaction was allowed to cool to room temperature and the crude material was extracted with EtOAc (50 mL) and washed with saturated NaHCO3 (3×50 mL). The organic layer was washed with brine (50 mL), dried over MgSO4, filtered and evaporated in vacuo to give an oily residue. The residue was purified by silica gel chromatography with 50% EtOAc/hexanes as eluant to give 500 mg (79.4% yield) of a yellow solid. Mp: 239-240° C. 1H NMR (DMSO-d6; 400 MHz): d 1.74 (s, 6), 2.63 (s, 3), 3.83 (s, 4), 7.44 (t, 1, J=2.4), 7.5 (t, 2, J=7.0), 7.80 (d, 2, J=7.1). MS m/z: 373.0 (M+1); 369.0, 371.0 (M−1).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe crude material was extracted with EtOAc (50 mL)
  3. washwashed with saturated NaHCO3 (3×50 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give an oily residue
  9. customThe residue was purified by silica gel chromatography with 50% EtOAc/hexanes as eluant

Sources & evidence

ORD record
ord-8e2ac0d092a54c018884fe788fa40636
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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