Diisopropylethylamine → HCID 178425512, compound

HRID 2047657Notes

Reaction equation

HRID 2047657 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[N:27]=[CH:26][C:25]([CH2:28][NH2:29])=[CH:24][CH:23]=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:25]2[CH:26]=[N:27][C:22]([CH3:21])=[CH:23][CH:24]=2)[N:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 52879146-Chloro-2-fluoropurineHCID 12214337(6-Methylpyridin-3-yl)methanamine

Product 1

HCID 178425512HCID 178425512, 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 (6-methylpyridin-3-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: 0.38 g (65%) δH CDCl3, 250 MHz) 2.44 (3 H, s, CH3), 3.66-3.57 (2 H, m, NHCH2), 4.63 (1H, s, br, NH), 7.25 (1 H, d, J 7.5, ArH), 7.71 (1 H, dd, J 2.5, 7.5, ArH), 8.14 (1 H, s, ArH), 8.49 (1 H, s, ArH), 9.07 (1 H, s, br, NH); δC (CDCl3, 250 MHz) 159.12 (C), 158.62 (C), 157.61 (C), 155.56 (C), 147.44 (CH), 146.99 (CH), 136.32 (C), 123.05 (2×CH), 119.42 (C), 41.64 (CH2), 18.47 (CH3); m/z 259.2 (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 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-d8697f1accbf41a88c589e6dbab8cf71
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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