Diisopropylethylamine → HCID 178426290, compound

HRID 2047673Notes

Reaction equation

HRID 2047673 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[C:23]([CH2:28][NH2:29])=[N:24][CH:25]=[CH:26][CH:27]=1>CCCCO>[F:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][NH:6]2)=[C:2]([NH:29][CH2:28][C:23]2[C:22]([CH3:21])=[CH:27][CH:26]=[CH:25][N:24]=2)[N:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514370(3-Methylpyridin-2-yl)methanamineHCID 52879146-Chloro-2-fluoropurine

Product 1

HCID 178426290HCID 178426290, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred solution of 6-chloro-2-fluoropurine (0.4 g, 2.3 mmol) in n-BuOH (50 ml) under an argon atmosphere at 0° C., was added DIEA (2.5 ml, 14.7 mmol) followed by (3-methylpyridin-2-yl)methanamine (0.36 g, 2.95 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 column chromatography on silica gel, eluted with CHCl3:MeOH (100:0→90:10), to afford the product as a white solid; Yield: 0.3 g (51%). δH (CDCl3, 500 MHz) 2.35 (3 H, s, CH3), 4.71 (3 H, m, NH and NHCH2), 7.24 (1 H, s, br, ArH), 7.63 (1 H, s, br, ArH), 8.28 (1 H, s, br, ArH), 8.38 (1 H, s, br, ArH); δC (CDCl3, 500 MHz) 161.03 (C), 158.49 (C), 154.77 (C), 152.16 (C), 144.86 (CH), 137.53 (CH), 137.14 (CH), 130.67 (C), 121.58 (CH), 118.73 (C), 42.87 (CH2), 18.16 (CH3); m/z 259.3 (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 8 h
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by gradient column chromatography on silica gel
  8. washeluted with CHCl3:MeOH (100:0→90:10)

Sources & evidence

ORD record
ord-56efd595b4e84695ad91b74e6013e2c8
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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