m-Toluidine → HCID 87676274, compound

HRID 227636Notes

Reaction equation

HRID 227636 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[C:19](=[O:26])[C:20](=[O:25])[C:21]=4OCC)=[CH:13][CH:12]=3)=[C:9]([CH2:27][CH3:28])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:29][C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33]>C(O)C>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[C:19](=[O:26])[C:20](=[O:25])[C:21]=4[NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[C:30]([CH3:29])[CH:31]=4)=[CH:13][CH:12]=3)=[C:9]([CH2:27][CH3:28])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 876759983-{[4-(4-Amino-6-ethylthieno[2,3-d]pyrimidin-5-yl)phenyl]amino}-4-ethoxy-3-cyclobutene-1,2-dione

Product 1

HCID 87676274HCID 87676274, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 344A (0.027 g, 0.068 mol) and 3-methylaniline (0.073 mL, 0.68 mmol) in ethanol (2 mL) was stirred at reflux for 48 hours and concentrated. The residue was purified by silica gel chromatography with 5% methanol/dichloromethane to provide 8 mg of the desired product. MS (ESI(+)) m/e 346 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.17 (t, J=7.46 Hz, 3H); 2.32 (s, 3H); 2.66 (q, J=7.12 Hz, 2H); 6.80-7.00 (m, 2H); 7.20-7.50 (m, 4H); 7.67 (d, J=8.48 Hz, 2H); 8.28 (s, 1H); 10.11 (s, 1H); 10.30 (s, 1H).

Workup

  1. temperatureat reflux for 48 hours
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-e37339060b3646e28bbd492cced09417
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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