1,4-Dibromobutane → HCID 58405764, compound

HRID 44888Notes

Reaction equation

HRID 44888 reaction equation
Cl.[NH2:2][N:3]1[C:12]2[N:11]=[C:10]([N:13]3[CH:17]=[CH:16][N:15]=[C:14]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=[CH:8][C:7]=2[N:6]([CH3:24])[C:5](=[O:25])[CH:4]1[CH2:26][CH3:27].Br[CH2:29][CH2:30][CH2:31][CH2:32]Br.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:26]([CH:4]1[N:3]([N:2]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:12]2[N:11]=[C:10]([N:13]3[CH:17]=[CH:16][N:15]=[C:14]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=[CH:8][C:7]=2[N:6]([CH3:24])[C:5]1=[O:25])[CH3:27]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 67260078HCID 67260078, compound

Product 1

HCID 58405764HCID 58405764, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

8-amino-7-ethyl-5-methyl-2-(2-phenyl-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one hydrochloride salt (Example 278, 28 mg, 0.073 mmol) was combined with 1,4-dibromobutane (0.05 mL, 0.42 mmol) and potassium carbonate (38 mg, 0.27 mmol) in 0.2 mL of CH3CN. This mixture was heated to 80° C. for 19 h, then filtered, washed with EtOAc, and the filtrate concentrated under reduced pressure. The residue was purified by HPLC to give the title compound. 1H NMR (CD3OD) δ: 8.01 (s, 2H), 7.73 (d, J=1.8 Hz, 1H), 7.70-7.50 (m, 5H), 4.43 (t, J=4.1 Hz, 1H), 3.36 (s, 3H), 2.98-2.83 (m, 2H), 2.83-2.70 (m, 2H), 2.12-1.95 (m, 2H), 1.60-1.40 (m, 4H), 0.79 (t, J=7.5 Hz, 3H); LCMS [M+H]: 404.1 m/z (M+H)+; ret. Time: 6.82 min (Analytical Method C).

Workup

  1. filtrationfiltered
  2. washwashed with EtOAc
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-397ae1b91e9c4494be5da0320b2e37a8
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

Loading…