Diisopropylethylamine → HCID 178425123, compound

HRID 2047655Notes

Reaction equation

HRID 2047655 reaction equation
Cl[C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.CCN(C(C)C)C(C)C.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][C:23]=1[CH2:29][NH2:30]>CCCCO>[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][C:23]=1[CH2:29][NH:30][C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 52879146-Chloro-2-fluoropurineHCID 289249021-(4,6-Dimethylpyridin-3-yl)methanamine

Product 1

HCID 178425123HCID 178425123, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred solution of 6-chloro-2-fluoropurine (0.83 g, 4.9 mmol) in n-BuOH (50 ml) under an argon atmosphere at 0° C., was added DIEA (2.5 ml, 14.7 mmol) followed by (4,6-dimethylpyridine-3-yl)methanamine (1 g, 7.35 mmol). The reaction mixture was stirred at this temperature for 1 h and then allowed to return to room temperature and stirred for 4 h, it was still seen incomplete, hence heated the reaction to 100° C. and left at that temperature for 2 h. The solvent was evaporated in vacuo and the residue was purified by gradient flash column chromatography on silica gel, eluted with CHCl3:MeOH (100:0→90:10), to afford the product as a white solid; Yield: 0.86 g (65%); δH (250 MHz, CDCl3) 2.35 (3 H, s, CH3), 2.39 (3 H, s, CH3), 4.61 (2 H, s, br, NHCH2), 7.07 (1 H, s, ArH), 8.13 (1 H, s, ArH), 8.33 (1 H, s, ArH), 8.69 (1 H, s, br, NH); δC (250 MHz, CDCl3) 161.2 (C), 158.57 (C), 156.08 (C), 150 (C), 148.08 (CH), 148.14 (CH), 147.9 (CH), 145.93 (C), 129.92 (C), 129.76 (C), 124.37 (CH), 41.7 (CH2), 23.17 (CH3), 18.14 (CH3); m/z 273.2 (M+H)

Workup

  1. customto return to room temperature
  2. stirringstirred for 4 h
  3. temperaturehence heated
  4. customthe reaction to 100° C.
  5. waitleft at that temperature for 2 h
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by gradient flash column chromatography on silica gel
  8. washeluted with CHCl3:MeOH (100:0→90:10)

Sources & evidence

ORD record
ord-388c49c04b414be6940e5df3211d8bed
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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