1-Butanol → HCID 178456855, compound

HRID 216880Notes

Reaction equation

HRID 216880 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1)[C:16]([C:22]([NH2:25])([CH3:24])[CH3:23])=[N:17]2.C(N(CC)C(C)C)(C)C.C(O)CCC>>[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1)[C:16]([C:22]([NH:25][C:2]1[N:10]=[CH:9][N:8]=[C:7]3[C:3]=1[N:4]=[CH:5][NH:6]3)([CH3:23])[CH3:24])=[N:17]2

Participants

5

Reactant 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 5287830Purine, 6-bromo-HCID 57707812HCID 57707812, compound

Product 1

HCID 178456855HCID 178456855, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromopurine (0.2423 g, 1.218 mmol), 2-(5-chloro-3-(3-fluoro-phenyl)quinoxalin-2-yl)propan-2-amine (0.3845 g, 1.218 mmol), and N,N-diisopropylethylamine (0.6363 mL, 3.653 mmol) in 1-butanol (7.000 mL, 1.218 mmol) was stirred at 100° C. After 62 h, the mixture was removed from the heat and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using 30% of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 as eluent to give N-(2-(5-chloro-3-(3-fluorophenyl)quinoxalin-2-yl)propan-2-yl)-9H-purin-6-amine as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.84 (1H, s), 8.12 (1H, dd, J=8.4, 1.0 Hz), 8.00 (2H, dd, J=7.5, 1.1 Hz), 7.80-7.91 (1H, m), 7.78 (1H, s), 6.88-7.19 (3H, m), 6.75 (1H, s), 6.41 (1H, s), 1.94 (6H, s); LC-MS (ESI) m/z 434.2 [M+H]+.

Workup

  1. customthe mixture was removed from the
  2. temperatureheat
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-9dde042c296e49f89b505a99f36c2e9f
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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