Diisopropylethylamine → HCID 178426369, compound

HRID 2047670Notes

Reaction equation

HRID 2047670 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]([CH2:28][NH2:29])[CH:25]=[C:24]([CH3:30])[N:23]=1>CCCCO>[CH3:21][C:22]1[CH:27]=[C:26]([CH2:28][NH:29][C:2]2[N:10]=[C:9]([F:11])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH:25]=[C:24]([CH3:30])[N:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 52879146-Chloro-2-fluoropurineHCID 135828191-(2,6-Dimethylpyridin-4-yl)methanamine

Product 1

HCID 178426369HCID 178426369, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred solution of 6-chloro-2-fluoropurine (0.4 g, 2.9 mmol) in n-BuOH (50 ml) under an argon atmosphere at 0° C., was added DIEA (2.5 ml, 14.7 mmol) followed by (2,6-dimethylpyridin-4-yl)methanamine (0.54 g, 4 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 8 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: 0.5 g (63%); δH CDCl3, 250 MHz) 2.48 (6H, s, 2×CH3), 3.65-3.54 (2 H, m, NHCH2), 4.61 (1 H, s, br, NH), 7.32 (2 H, s, ArH), 7.84 (1 H, s, ArH)), 9.05 (1 H, s, br, NH); δC (CDCl3, 250 MHz) 159.2 (C), 156.62 (C), 156.61 (C), 155.46 (C), 146.92 (CH), 136.3 (C), 122.05 (2×CH), 119.48 (C), 41.6 (CH2), 18.06 (2×CH3)

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 8 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-c6b841a5a5304758aaba8e00c71d5f70
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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